SYNTHESIS AND STEREOCHEMISTRY OF OPTICALLY-ACTIVE TELLURONIUM YLIDES

被引：21

作者：

KAMIGATA, N

MATSUHISA, A

TAKA, H

SHIMIZU, T

机构：

[1] Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Hachioji

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 07期

关键词：

D O I：

10.1039/p19950000821

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoisomeric mixtures of 1-{4-[(-)-menthyloxycarbonyl]phenyl(methyl)telluroniumyl}-4,4-dimethyl-2,6-dioxocyclohexan-1-ide dia.-5a, b and 1-{4[(-)-methyloxycarbonyl]phenyl(2,4,6-triisopropylphenyl)telluroniumyl}-4,4-dimethyl-2,6-dioxocyclohexan-1-ide dia.-12a, b have been synthesized. Optical resolution by the fractional recrystallization of dia.-5a, b and dia.-12a, b from hexane-dichloromethane gave the optically active(+)(Te)-telluronium ylides (+)(Te)-5a and (+)(Te)-12a as stable crystals, respectively. The absolute configuration of(+)(Te)-5a has been determined to be R based on the CD spectrum. The kinetics for the epimerization by pyramidal inversion of the optically active telluronium ylide (+)(Te)-12a have been studied.

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页码：821 / 827

页数：7

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