Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

Abstract

A process for the synthesis of P-chiral triarylphosphine sulfides via sequential Pd-catalyzed stereospecific P–C coupling reactions of P-chiral precursors prepared by enzymatic desymmetrization was developed. Three independent aryl substituents could be introduced onto the P atom by the sequential P–C couplings under mild conditions while retaining the high enantiopurity.

DOI： 10.1055/a-1873-3530

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Authorship：Lead author,　Corresponding author   Publishing type：Research paper (scientific journal)  

Organophosphorus compounds play several essential roles in organic chemistry, such as valuable ligands in transition metal catalysis and functional materials. We have developed versatile organophosphine syntheses via Pd-catalyzed P-C cross-coupling reactions in the course of our study using silylphosphines. Up to three aryl groups can be selectively incorporated into the same phosphorus atom in a stepwise manner. In addition, we found the formation of phosphorus-ylide containing phosphacycles, λ5-phosphinines, during the extension of silylphosphine chemistry.

DOI： 10.1080/10426507.2021.2008932

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

DOI： 10.1021/acs.organomet.1c00314

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Phosphine sulfides are the pentavalent derivatives of organophosphines and are usually used as synthetic intermediates of organophosphines for their isolation as protected analogs because of the stability toward oxidation. Recently, several applications of phosphine sulfides have been disclosed as functional materials, organocatalysts, ligands, and extractants. In addition, several synthetic uses of phosphine sulfides have also developed, in which the thiophosphinyl group plays an essential role. This Highlight Review covers recent applications and syntheses of organophosphine sulfides.

DOI： 10.1246/cl.200651

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Language：English   Publishing type：Research paper (scientific journal)  

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Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tetlet.2020.151724

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/chem.201902668

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201902668

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Nature Publishing Group  

Abscisic acid (ABA) is the main phytohormone involved in abiotic stress response and its adaptation, and is a candidate agrichemical. Consequently, several agonists of ABA have been developed using the yeast two-hybrid system. Here, we describe a novel cell-free-based drug screening approach for the development and validation of ABA receptor agonists. Biochemical validation of this approach between 14 ABA receptors (PYR/PYL/RCARs) and 7 type 2C-A protein phosphatases (PP2CAs) revealed the same interactions as those of previous proteome data, except for nine new interactions. By chemical screening using this approach, we identified two novel ABA receptor agonists, JFA1 (julolidine and fluorine containing ABA receptor activator 1) and JFA2 as its analog. The results of biochemical validation for this approach and biological analysis suggested that JFA1 and JFA2 inhibit seed germination and cotyledon greening of seedlings by activating PYR1 and PYL1, and that JFA2 enhanced drought tolerance without inhibiting root growth by activating not only PYR1 and PYL1 but also PYL5. Thus, our approach was useful for the development of ABA receptor agonists and their validation.

DOI： 10.1038/s41598-018-22538-9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

© 2018 American Chemical Society. A practical synthesis of a variety of λ5-phosphinines, which show distinct fluorescence both in solution and solid state, is described. Both C4-selective electrophilic substitutions and the following conversions realized an easy preparation of a wide range of derivatives having several substituents for electronic modification, which provides the potential for fine-tuning of the photophysical properties.

DOI： 10.1021/jacs.7b13018

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

The development of a versatile process for phosphine synthesis has attracted considerable interest because organophosphines are indispensable for organic synthesis. Previously, we developed a Pd-catalyzed P–C coupling reaction for hydroxymethylphosphine sulfide derivatives with various aryl iodides as a method for preparing a variety of triarylphosphine derivatives. However, the catalyst system for aryl iodides did not activate aryl bromides and triflates, which are more readily available than aryl iodides. Herein, we report a new and effective catalyst system for the P–C coupling of various aryl bromides and triflates with hydroxymethylphosphine sulfides. An application of the new method was demonstrated with the sequential synthesis of an unsymmetrically substituted triarylphosphine sulfide by using multiple couplings of an orthogonally protected precursor.

DOI： 10.1002/ejoc.201701706

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

Nuclear factor-κB (NF-κB) proteins are transcription factors that play key roles in regulating most immune responses and cell death. Constitutively active NF-κB has been shown to exhibit chemoresistance by inducing anti-apoptosis in tumor cells. Multiple myeloma is known as a constitutive NF-κB activating disease, and the proteasome inhibitor bortezomib is used to treat multiple myeloma and mantle cell lymphoma. We demonstrate here that DANFIN (N,N′-bis-(2,4-dimethyl-phenyl)-ethane-1,2-diamine) functions as an inhibitor of the p65 family proteins and induces chemosensitization to bortezomib in multiple myeloma. DANFIN was found to be an inhibitor of interactions between p65 and IκBα without the inhibition of the DNA binding activity of the p65 protein. In addition, DANFIN affected the IκBα binding region in Rel Homology Domain (RHD) and suppressed the nuclear translocalization of the p65 protein in cells. Furthermore, in multiple myeloma cells, DANFIN suppressed the expression level of NF-κB target genes and induced apoptosis. The combination therapy of DANFIN with bortezomib dramatically enhanced the apoptosis of multiple myeloma cells and indicated a remarkable anti-tumor effect in a multiple-myeloma xenograft mouse model.

DOI： 10.1016/j.bbrc.2017.12.142

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Three synthetic procedures have been developed for a new class of phosphorus ylide containing conjugate heterocycles, 3oxo-lambda(5)-benzophospholes. The key to the formation of the heterocycle is unusual intramolecular acylation of a phosphorus ylide forming an endocyclic ylide. Several types of 2-substituted benzophospholes are synthesized, some of which show fluorescence.

DOI： 10.1246/cl.170758

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

We have previously reported hydrodeoxygenation (HDO) of phenols to form cyclohexanes at 110 degrees C under ambient H-2 pressure by using Pt/H-ZSM-5 catalyst and octane as a solvent; however, the low solubility of some phenols in octane is a major problem for expanding the scope of this reaction. Herein, we report that Pt/H-beta catalyzes the HDO using ester solvents which dissolve a wide range of phenols. The difference in HDO performance between the catalyst systems, Pt/H-beta in esters and Pt/H-ZSM-5 in octane, was also investigated. Furthermore, we have demonstrated that HDO of a phenol proceeds at 85 degrees C by Pt/H-beta in an ester solvent.

DOI： 10.1002/slct.201700696

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

An air- and moisture-stable N-heterocyclic carbene Ni(II) complex bearing bis(cyclopentadienyl) ligands was found to be an effective precatalyst for the dehydrogenative silylation of alcohols with hydrosilanes. Various aryl and alkyl alcohols were silylated in the presence of the Ni catalyst (1-4 mol %) in toluene at 110 degrees C, giving the corresponding silyl ethers in 59-99% isolated yields. Time-course studies revealed that the reaction has an induction period, during which the Ni(II) complex would be reduced to catalytically active Ni(0) species. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2015.04.069

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

The hydrodeoxygenation of various phenols to form cyclohexanes was achieved at 110 degrees C under an H-2 atmosphere at ambient pressure using a Pt/H-ZSM-5 catalyst and octane as the solvent.

DOI： 10.1039/c5cc05607a

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Enantioselective reduction of acylphosphines, after precomplexation with borane, proceeded smoothly in the presence of a chiral oxazaborolidine catalyst and catecholborane. alpha-Hydroxyalkylphosphine products were obtained as phosphineborane complexes in good yield and enantioselectivity. One of the products of the enantioselective reduction was successfully applied as an optically active phosphine ligand for asymmetric catalysis after suitable derivatization.

DOI： 10.1021/ol5024757

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© 2014, IS Publications. The functionalized myo-inositols, 1,4,5-triphosphoinositol and posphatidylinositol (3,4,5)-triphosphate, are intracellular signaling molecules. Using a one-step regioselective functionalizing method, we synthesized 1-mono-O- and 1,3-di-O-substituted-myo-inositols and then evaluated their in vitro antiproliferative effects on two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The 1,3-di-O-substituted-myo-inositol, containing menthyloxycarbonyl, tert-butyldiphenylsilyl ether (TBDPS), and triisopropylsilyl ether (TIPS), potently inhibited the growth of both types of tumor cells, and exhibited IC50 values of 2.74, 1.15, and 1.70 μM for HCT-116 cells and 9.89, 8.20, and 8.49 μM for HL-60 cells, respectively. The cytotoxic effects of the three disubstituted-myo-inositols on HL-60 cells were dose- and time-dependent, and these molecules also activated caspase-3, which is used as an index of cell apoptosis, within the cells. These findings indicate that 1,3-disubstituted, but not 1-monosubstituted, myo-inositols activated caspase-3 and prevented the proliferation of HCT-116 and HL-60 tumor cells.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

DOI： 10.1002/ajoc.201300163

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Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively 1,3-di-O-substituted or racemic 1-O-substituted derivatives, depending on a quantity of reagents and reaction time. α-Unbranched alkanoic acid anhydrides in LiCl/DMA in the presence of triethylamine were suitable for acylation of myo-inositol, in contrast to the fact that acylation using alkanoyl chlorides in aprotic polar solvents generally does not proceed well due to decomposition of the reagents by the reaction with the solvents. © 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2013.03.109

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Practical and versatile syntheses of tertiary phosphine derivatives have been achieved by palladium-catalyzed deformylative P-C cross-coupling reactions of hydroxymethylphosphine derivatives. Sequential couplings of orthogonally protected precursors provide a simple and practical route toward a variety of tertiary phosphine derivatives having aryl substituents in any combination.

DOI： 10.1021/ol303448j

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Language：Japanese   Publisher：(公社)日本薬学会  

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A new class of phosphorus-ylide containing conjugate heterocycle was isolated from a mixture of colored products of the reaction of a silylphosphine and dimethyl acetylenedicarboxylate. The structure was determined and the selective synthesis was developed. The indigo-like bis-phosphole structure appears a green to blue color, which is derived from the low energy-gap of the phosphole.

DOI： 10.1021/jo1004235

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

Organophosphines play an important role in the field of organic synthesis, especially as ligands in transition metal catalysis. However, the synthesis of organophosphines with various functional groups still has many difficulties due to limitations in phosphorus-carbon bond formation. In this review, recent advances in the syntheses of organophosphines having various functional groups by using silylphosphines under mild conditions are described. Sterically protected silylphosphines are effectively applied to selective formations of several types of carbon-phosphorus bond, via three types of adequate activations; activation of a phosphorus-silicon bond of a silylphosphine by means of a fluoride, nucleophilic attack to the electrophile activated by a Lewis acid, and a transition-metal catalyzed activation of phosphorus-silicon bond. One successful application of a step-wise functional phosphine synthesis is also described.

DOI： 10.5059/yukigoseikyokaishi.68.614

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

Organophosphines play an important role in the field of organic synthesis, especially as ligands in transition metal catalysis. However, the synthesis of organophosphines with various functional groups still has many difficulties due to limitations in phosphorus-carbon bond formation. In this review, recent advances in the syntheses of organophosphines having various functional groups by using silylphosphines under mild conditions are described. Sterically protected silylphosphines are effectively applied to selective formations of several types of carbon-phosphorus bond, via three types of adequate activations; activation of a phosphorus-silicon bond of a silylphosphine by means of a fluoride, nucleophilic attack to the electrophile activated by a Lewis acid, and a transition-metal catalyzed activation of phosphorus-silicon bond. One successful application of a step-wise functional phosphine synthesis is also described.

DOI： 10.5059/yukigoseikyokaishi.68.614

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

A self-condensation of aldehydes has been conveniently accomplished by the catalytic action of lysine in water or a solvent-free system under specific emulsion conditions to give alpha-branched alpha,beta-unsaturated aldehydes in good yields.

DOI： 10.1039/b918349c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

1,3,5-Triazines bearing one, two or three diphenylphosphanyl group(s) were selectively synthesized from cyanuric chloride by the one-pot step-by-step addition of silylphosphane and other nucleophiles. Mono- and diphosphanyltriazines with a variety of substituents on the triazine ring could be easily prepared in good yields. The Pd complexes of mono- and diphosphanyltriazine were isolated, and the crystal structures were determined. Polymer-supported and water-soluble ligands were prepared. The Mizorogi-Heck reaction and the Suzuki-Miyaura coupling reaction using the phosphanyltriazine-Pd catalysts are described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

DOI： 10.1002/ejoc.200900429

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Functionalizations of hydroxy groups of myo-inositol were usually nonselective due to its poor solubility. By dissolving myo-inositol in DMSO or LiCl-N,N-dimethylacetamide, we have achieved regioselective acylation, silylation, sulfonylation, phosphinylation to give the corresponding 1,3-di-O-substituted products in good yields.

DOI： 10.1055/s-0029-1217809

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JOHN WILEY & SONS INC  

This paper describes the recent advances in the syntheses of organophosphines by forming several types of phosphorus-carbon bonds via activation of the phosphorus-silicon bond of silylphosphines. In this account, the activation methods are classified into three types, nucleophile-induced activations, reactions with Lewis acid-activated electrophiles, and transition metal catalyzed reactions. Nucleophile-induced activations of silylphosphines, especially by a fluoride, generated a reactive phosphide equivalent for selective formation of a P-C bond Silylphosphines also reacted selectively with Lewis acid-activated electrophiles. The Lewis acid mediated/catalyzed additions and substitutions, to form sp(3)-carbon-phosphorus bonds including an asymmetric reaction, are described. Several important types of transition metal catalyzed reactions of silylphosphines are also mentioned in this account. Selective formation of a P-C bond is achieved through these activations to produce a variety of functional organophosphines including optically active ones (C) 2009 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 9: 236-245, 2009: Published online in Wiley InterScience (www.interscience.wiley com) DOI 10.1002/tcr.200900011

DOI： 10.1002/tcr.200900011

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

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Triethylaluminum-catalyzed/mediated addition of a silylphosphine to aldehydes and epoxides is described. Organophosphines containing a silyloxy group at the alpha- or beta-position on the alkyl substituent are successfully prepared in good yields.

DOI： 10.1021/jo701330q

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

An enantioselective silylphosphination of aldehydes mediated by a chiral Lewis acid is described. The chiral Lewis acid prepared from TiCl4 and diisopropyl L-tartrate successfully induced chirality in the addition of silylphosphine to several aldehydes, to give the corresponding alpha-hydroxyalkylphosphine derivatives in good yields and good enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetasy.2007.03.033

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A synthesis of highly substituted alkenylphosphines by Lewis acid-mediated silylphosphination of substituted propiolates is described. The addition proceeded smoothly to give the corresponding acrylates, where the phosphino group attached at the beta and the silyl group located at the alpha position of the resulting acrylate, in exclusively syn-stereochemistry.

DOI： 10.1246/cl.2007.634

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

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A novel rhodium-catalyzed hydrophosphination of alkynes using a silylphosphine as a phosphino group source is described. A variety of alkynes, both terminal and internal ones with aryl, alkyl, and carboxyl groups, gave the corresponding alkenylphosphines in a highly regioselective and syn-selective manner. Alkenes with an electron-withdrawing group also gave the corresponding adducts in good yields.

DOI： 10.1021/jo061739f

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Language：English   Publisher：Symposium on the chemistry of natural products  

DOI： 10.24496/intnaturalprod.2006.0__P-268_

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A novel CsF-catalyzed three-component coupling reaction of a silylphosphine, activated alkenes and aldehydes is described. Multi-functional phosphines were obtained by forming both carbon-phosphorus and carbon-carbon bonds in good yields under mild conditions. (c) 2005 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2005.05.128

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The bis(dibutylstannylene) derivative of 1,2-cyclohexylidene -myo-inositol, reacted with (S)-O-acetylmandeloyl choride and diphosphate tetraesters to give 3,6-dimandelate and 3-phosphate, respectively. Using the stannylene methodology for the optical resolution and regioselective phosphorylation of the ketal, a concise synthesis of phosphatidyinositol with the natural configuration was accomplished. (C) 2004 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2004.11.055

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Regioselective phosphination of carbon-carbon unsaturated bonds by a fluoride-mediated reaction of silylphosphines is described. Alkenes and alkynes having a directing group, such as an aromatic or a carbonyl group, reacted to form a carbon-phosphorus bond under mild conditions. When an anhydrous fluoride source was applied in the presence of an electrophile, the corresponding three-component coupling product was obtained. (C) 2004 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2004.10.098

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A general and practical method for the synthesis of Te-aryl phosphorotellurates is described. A series of Te-aryl phosphorotellurates could be synthesized in good to excellent yields by the reaction of dialkyl, diaryl and trialkyl phosphites with arenetellurynyl and arenetellurenyl halides. A phenylphosphonotelluroate and a phosphorotelluramidate were also prepared by a similar procedure.

DOI： 10.1055/s-2004-822386

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Contrary to the usually accepted phenomena, an optically heterogeneous 1:1 diastereomixture of DS and LS and a racemate of LS and DR obtained, respectively, from a racemic myo-inositol derivative and (S)- and racemic O-acetylmandelic acid formed stronger organogels, especially with aromatic fluids, than those formed from homochiral isomers, DS and LS. One of the plausible reasons for the formation of the stronger diastereomeric gel is shown to be the complementary interaction of two diastereomers.

DOI： 10.1021/ol049737

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A novel activation mode of silylphosphines and an application of that to silylation of alcohols were described. Silylphosphines were found to be instantly activated by means of DEAD and PPTS to form reactive silyl cation equivalents. By using the activated species, silylation of alcohols successfully proceeded under mild acidic condition. (C) 2003 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2003.12.053

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The X-ray crystal structure of D-1,4-di-O-(O-acetylmandeloyl)-2,3:5,6-di-O-isopropylidene-myo-inositol showed two different conformations for different acetylmandelate groups. A comparison of its conformation in solution with that in the solid is made by the use of H-1 NMR. The observed anisotropic shielding effect is rationalized based on these conformational studies. This study cautions the use of O-acetylmandelate as CAR for sterically crowded and conformationally locked alcohols. (C) 2003 Published by Elsevier Ltd.

DOI： 10.1016/j.tetasy.2003.10.012

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Chemical resolution of a versatile starting material, 1,2-O-cyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)- myo-inositol, which is used to access naturally occurring inositol phosphates and phosphatidylinositol phosphates, is described. Starting from both D- and L-enantiomers of the material, the synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate [PtdIns(3,5)P2] has been conveniently accomplished via convergent routes. One of the key reactions in the synthetic procedure was the regioselective phosphorylation of suitably protected 1,2,4-triol derivatives of inositol. Phosphorylation of the triol attempted in a 1:12 (v/v) pyridine/CH2Cl2 mixture did not proceed at all, whereas in an optimized solvent system, pyridine/CH2Cl2 (1.1:1, v/v), the reaction afforded 68% of the desired 1-O-phosphate as a single product. Further investigation by H-1 NMR spectroscopy indicated that the reactivity of the three OHs on 1,2,4-triol derivatives is governed by intermolecular hydrogen bonding, which may be disrupted by an increase in the proportion of pyridine in the reaction solvent. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

DOI： 10.1002/ejoc.200300517

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Language：Japanese   Publisher：Symposium on the chemistry of natural products  

Inositol phosphates and phosphoinositides are now well known physiologically important molecules mainly as second messengers for intracellular signal transduction. As part of our efforts to establish convenient and practical syntheses of them, here we report selective phosphorylation of 3,4-diol, 2,3,6-triol and 3,4,5,6-tetrol derivatives of myo-inositol, using the phosphite-pyridinium tribromide method developed by us, and discuss also practical resolution of 1,2-cyclohexylidene-myo-inositol. Distannylene derivative transformed in situ from ketal 1 smoothly reacted with chiral acetylmandeloyl chloride to give L-3,6-dimandelate (42%) and D-products consisting of 3-mono ester (20%) as well as 3,6-ester (10%), that could be easily separated to optically pure products. In a similar manner, phosphorylation of 1 with pyrophosphate in place of the acid chloride afforded 2 in excellent yield. Diol 3 was treated with glycerol phosphite in the presence of pyridinium tribromide and 2,6-lutidine, resulting in the smooth and selective formation of 3-phosphate 4 in 88%. The product was unexpectedly deprotected at once under hydrogenolysis conditions using commercial AcOEt without purification as a solvent, giving PI(4,5)P2 with palmitoyls. Both enantiomers resolved were converted to triols 5 and 7, respectively. These triols were subjected to the same phosphorylation procedure as above, to afford exclusively 3-O-phosphorylation products 6 and 8, which were then deprotected in two-step procedure to give the same product, PI(3,5)P2. It should be noted that a pyridine-CH_2Cl_<2> (1:1) mixed solvent system was needed for the phosphorylation to take place. The role of pyridine is presumably to dissociate the aggregation state of the triols because they extraordinarily associate each other, as indicated by nmr analysis.

DOI： 10.24496/tennenyuki.45.0_601

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The reactivity of 3 and 4-OH in 3,4-diol myo-inositol derivatives were observed through the phosphorylation, acylation and silylation. The results indicated that 3-OH is much more reactive than 4-OH, giving regiospecifically 3-mono-functionalized products. This investigation provided a concise methodology for the synthesis of natural D-form of PtdIns(4,5)P2 and D-Ins(1,4,5)P3 from L-1,2-O-cyclohexylidene-3,4-O-(tetraisopropyl disiloxane-1,3-diyl)-myo-inositol. (C) 2003 Elsevier Ltd. All rights reserved.

DOI： 10.1016/S0040-4020(03)01212-2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

The synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate [PtdIns(3,5)P2] has been conveniently accomplished via convergent routes starting from both enantiomers, 1,2-O-cyclohexylidene-myo-inositol. The synthetic strategy involves completely regioselective phosphorylation of 3,4-diol and 2,3,6-triol of the suitably protected inositols with the corresponding phosphite in the presence of pyridinium tribromide and 2,6-lutidine, resulting in the formation of 3-O-phosphorylated products, respectively.

DOI： 10.1246/cl.2003.724

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

An efficient method for the resolution of 1,2:4,5-di-O-isopropylidene-myo-inositol has been developed. The diketal was converted to diastereomeric 3,6-di-O-mandelates by the reaction with (S)-O-acetylmandeloyl chloride. Both the diastereomers could be separated by sequential crystallization in multi-gram quantities. The enantiomers of the diol were obtained by removal of the chiral auxiliaries. Also the trans-isopropylidene was cleaved efficiently to obtain another pair of chiral diols. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0957-4166(03)00402-6

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Dipalmitoylphosphatidylinositol 4,5-bisphosphate was conveniently synthesized via the regioselective phosphorylation Of L-1-2-O-cyclohexylidene-5,6-di-O-(o-xylylene phosphoryl)myo-inositol derived from 1,2-O-cyclohexylidene-3,4-O-(tetraisopropyldisiloxane- 1,3-diyl)-myo-inositol.

DOI： 10.1246/cl.2003.46

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

To compare the synthetic utility of cyclic xylylene N,N-diethylphosphoramidite and its acyclic analog, dibenzyl ester, both phosphites derived from them with dipalmitoylglycerol were subjected to the selective phosphorylation at the OH-3 position in 1,2:4,5-di-O-cyclohexylidene-myo-inositol in the presence of pyridinium tribromide, and the cyclic version showed to be much superior to the acyclic. The 3-O-phosphorylated product was conveniently converted into phosphatidylinositol 4-phosphate.

DOI： 10.1246/cl.2002.292

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

To compare the synthetic utility of cyclic xylylene N,N-diethylphosphoramidite and its acyclic analog, dibenzyl ester, both phosphites derived from them with dipalmitoylglycerol were subjected to the selective phosphorylation at the OH-3 position in 1,2:4,5-di-O-cyclohexylidene-myo-inositol in the presence of pyridinium tribromide, and the cyclic version showed to be much superior to the acyclic. The 3-O-phosphorylated product was conveniently converted into phosphatidylinositol 4-phosphate.

DOI： 10.1246/cl.2002.292

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Language：English   Publishing type：Research paper (international conference proceedings)  

DOI： 10.1080/10426500213329

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Acetals, including ketals, were smoothly cleaved by the action of pyridinium poly(hydrogen fluoride) without addition of water or an alcohol in an anhydrous solvent. (C) 2001 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(01)00808-5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The isolation of a new fullerene dimer, C122H4, and its structural characterization by C-13 NMR and H-1 NMR spectroscopy and by UV/vis and IR spectroscopy are reported. The structure of this dimer consists of two fullerene cages, which are directly connected through two C-C bonds and two methylene bridges. Consequently, adjacent hexagonal faces of the two fullerene cages are arranged in a face to face manner. Molecular orbital calculations indicate that the proximity of the fullerene cages results in significant through space overlap in both the HOMO and LUMO. As a consequence of this overlap, the electrochemistry of the dimer shows electronic communication with stepwise reduction of each cage.

DOI： 10.1021/jo991676j

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Enantiopure 2-[2-(diphenylphosphino)phenyl]oxazoline derived from a non-natural chiral aminoalcohol, cis-2-amino-3,3-dimethyl-1-indanol, was found to be an efficient ligand for the palladium-catalyzed asymmetric Heck reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0957-4166(00)00157-9

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Chiral imines, derived from (1S,2R)-2-methoxy-1,2-diphenylethylamine and aromatic aldehydes, reacted with ester enolates prepared from ketene silyl acetals and methyllithium to give beta-lactams in good yields with high diastereoselectivity. This method provides a useful and simple route for the construction of optically active beta-lactam skeletons.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Convenient access to cyclopentenones is provided by catalytic intra- and intermolecular Pauson - Khand reactions in the presence of octacarbonyldicobalt and tributylphosphane sulfide. In contrast to other reactions of this type, they proceed under mild conditions (70°C, 1 atm CO), and commercially available [Co2(CO)8] can be used without further purification.

DOI： 10.1002/(SICI)1521-3773(20000204)39:3<631::AID-ANIE631>3.0.CO;2-B

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Reaction of an anti head-to-tail 4-chlorocoumarin dimer with amines afforded benzopyranocoumarin derivatives in high yields; the reaction is quite different from the expected reaction of coumarin dimer derivatives with amines. On the basis of spectral information, a possible reaction mechanism is proposed through a tandem lactone ring-opening reaction, elimination, cycloreversion of cyclobutene, addition-elimination, and Michael addition. (C) 1999 Elsevier Science Ltd, All rights reserved.

DOI： 10.1016/S0040-4039(99)01488-4

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Phosphine sulfides were found to be effective as a ligand in the palladium(II)-catalyzed bisalkoxycarbonylation of olefins. Aromatic olefins and vinylsilanes were converted into the corresponding succinates in high yields under mild conditions. Enantioselection was observed when chiral bisphosphine sulfides were used as ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(98)01637-2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Phosphine sulfides were found to be effective as a ligand in the palladium(II)-catalyzed bisalkoxycarbonylation of olefins. Aromatic olefins and vinylsilanes were converted into the corresponding succinates in high yields under mild conditions. Enantioselection was observed when chiral bisphosphine sulfides were used as ligands. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(98)01637-2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Tripodal hexadentate ligands, having three 8-hydroxyquinolyl or 2-methyl-8-hydroxyquinolyl groups as binding sites, were successfully prepared from the corresponding tris(isobutenyl 8-quinolyl ether) via the Claisen rearrangement. The 2-methyl-8-hydroxyquinolyl derivative exhibited binding ability for several kinds of trivalent metal cations to form 1:1 complexes, and showed selective extractability for Ga3+ among trivalent cations of Group 13 elements. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(98)01277-5

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A novel tripodal hexadentate ligand, consisting of three catechol units, three isobutenyl ether arms, and one aromatic core, was synthesized through four steps, in which the Claisen rearrangement was included as the key step. The hexadentate ligand formed a 1:1 complex with iron(III) trichloride hexahydrate with an equilibrium constant (conditional) of 6.3 x 10(4) M-1 in acetonitrile in the presence of 2,4,6-trimethylpyridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(98)01278-7

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A novel optically active bisphosphine ligand CDP containing a C-2-symmetric cyclobutane ring was prepared from an enantiopure anti head-to-head coumarin dimer. CDP was successfully applied to the rhodium-catalyzed asymmetric hydrogenation of arylenamides, affording the corresponding amides up to 93% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0957-4166(98)00185-2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

A highly regioselective C-C bond cleavage of the cyclopropane rings occurs in substituted allenylcyclopropanes in the presence of cationic rhodium(I) complexes. Thus, ring expansion of readily accessible allenylcyclopropanes can be achieved to give 3-methylenecyclopentenes, which could have applications as multifunctional synthetic building blocks.

DOI： 10.1002/(SICI)1521-3773(19980403)37:6<837::AID-ANIE837>3.0.CO;2-R

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Conjugated enediyne compounds were synthesized by the palladium-catalyzed bis-alkynylation reaction of propargylic carbonates with terminal alkynes. An unsymmetric enediyne was also synthesized by successive addition of two different alkynes. (C) 1997 Elsevier Science Ltd.

DOI： 10.1016/S0040-4039(97)01435-4

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Novel copolymers, poly(1,4-oxybisphenylene fullerenobisacetamide-co-1,4-oxybisphenylene isophthalamide)s, which contained [60]fullerene in the main chain, were synthesized by the direct copolycondensation of a mixture of [60]fullerenobisacetic acid and isophthalic acid with 4,4'-diaminodiphenyl ether in the presence of triphenylphosphite and pyridine. Light scattering measurements for the copolymers showed a weight-average molecular weight Mw of about 5-6x10(4). The UV-visible spectra of the copolymers exhibited the characteristics of the parent fullerene derivative. The absorption edge red-shifted from 370 nm for poly(1,4-oxybisphenylene isophthalamide) to about 700 nm for the copolymers.

DOI： 10.1246/cl.1997.1037

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GORDON BREACH SCI PUBL LTD  

A new chiral (beta-aminoalkyl)phosphine, (1R,2S)-[2(N,N-dimethylamino)-1,2-diphenylethyl]diphenylphosphine (ADPEP), was prepared from enantiomerically pure amino alcohol, erythro-2-amino-1,2-diphenylethanol (ADPE). Substitution of the hydroxy group by a diphenylphosphino group proceeded with retention of the stereochemistry, presumably via an aziridinium ion intermediate formed by neighboring group participation of the amino group at beta-position. ADPEP was used in nickel- or palladium-catalyzed asymmetric cross-coupling reaction of 1-phenylethylmagnesium chloride with alkenyl bromides. The coupling products with 71% ee and 94% ee were obtained in the reactions with vinyl bromide and with (E)-beta-styryl bromide, respectively.

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

An intramolecular cycloisomerization occurred upon, adding a tertiary amine N-oxide to alkyne-cobalt complexes, derived from 3-sila 1,7-enynes and dicobalt octacarbonyl. As a result, eight-membered cyclic dienylsilanes were obtained by a regioselective insertion of the alkynyl group into the C(1)-H bond.

DOI： 10.1021/om9606294

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The dehydration of a carboxylic acid and an amine to form an amide linkage was performed by the use of a new water-compatible dehydrating agent, 2,2-dichloro-5-(2-phenylethyl)-4-(trimethylsilyl)-3-furanone (DPTF). The application of this new agent to the peptide bond formation is also described. Copyright (C) 1996 Elsevier Science Ltd

DOI： 10.1016/0040-4039(96)01712-1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JOHN WILEY & SONS LTD  

(alpha-Aminoalkyl)samarium(III) is generated on treatment of a tertiary amine having a pendant o-iodobenzyl group on the nitrogen atom with samarium(II) iodide (SmI2) in tetrahydropyran containing hexamethylphosphoramide. Deuterium incorporation experiments demonstrate that the reaction proceeds via a delivery of a radical center from the pendant benzyl group to the alpha-position of nitrogen and the following one-electron transfer from SmI2 to the delivered radical, Subsequent nucleophilic addition of (alpha-aminoalkyl)samarium(III) to various electrophiles, such as enolizable ketones, isocyanate and isocyanide, furnishes the C-C bond formation products in good yields, The pendant benzyl group of the product can be readily removed by hydrogenolysis to give the corresponding secondary amine, Therefore, the present reaction provides a useful synthetic process for a variety of nitrogen-containing compounds including beta-amino alcohols and alpha-amino acid derivatives, disclosing a new method for metalation and C-C bond formation.

DOI： 10.1002/aoc.590090505

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jo00104a058

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG  

Various alkynylsilanes are synthesized by samarium-mediated coupling reactions of ethynylsilanes with haloalkanes including alpha- and beta-branched ones.

DOI： 10.1055/s-1994-22784

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Language：English   Publishing type：Research paper (scientific journal)  

Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates α-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bond formation products in good yield. © 1992 American Chemical Society.

DOI： 10.1021/jo00029a001

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Treatment of a tertiary amine having a pendent o-iodobenzyl group on nitrogen with SmI2 generates alpha-amino organosamarium, which reacts with electrophiles giving the corresponding C-C bound formation products in good yield.

DOI： 10.1021/jo00029a001

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

DOI： 10.1021/jo00026a035

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DOI： 10.1002/anie.199114961

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Boric acid initiates the formation of coronand 1 from 2, providing the framework necessary for the strong complexation of alkali metal ions. This approach to the synthesis of the macrocyclic host allows a greater flexibility than the standard preorganization method. A bicyclic coronand is also obtained by this strategy. M = K, Na. (Figure Presented.) Copyright © 1991 by VCH Verlagsgesellschaft mbH, Germany

DOI： 10.1002/anie.199114961

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