STEREOSELECTIVE CONSTRUCTION OF QUATERNARY CARBON CENTERS - SYNTHESIS OF OPTICALLY-ACTIVE GAMMA,GAMMA-DISUBSTITUTED GAMMA-BUTYROLACTONES

被引：16

作者：

BLOCH, R

BRILLET, C

机构：

[1] Laboratoire des Carbocycles (Associé au C.N.R.S.), Institut de Chimie Moléculaire d'Orsay Bât. 420, Université de Paris-Sud

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80463-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An unusually strong solvent effect has been observed on the diastereoselectivity of nucleophilic additions of bromoalkylmagnesium compounds to the lactols 2 and 3, allowing the formation of pure diastereoisomers of 1,4-diols. Homochiral gamma,gamma-disubstituted gamma-butyrolactones could then be obtained after oxidation of these diols followed by a retro Diels-Alder reaction as illustrated by the synthesis of S-(+)-4,5-dimethyl-4-hexanolide.

引用

页码：797 / 800

页数：4

共 13 条

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