STEREOCONTROLLED REACTIONS INDUCED BY A THERMOLABILE GROUP - SYNTHESIS OF OPTICALLY-ACTIVE 1,3-DIOLS

被引：21

作者：

BLOCH, R

BORTOLUSSI, M

GIRARD, C

SECK, M

机构：

[1] U.R.A. 478, Institut de Chimie Moléculaire d'Orsay, Bât. 490 Université de Paris-Sud

来源：

TETRAHEDRON | 1992年 / 48卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)89007-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Wittig Horner-Michael reactions of phosphonates with optically active lactol 1 lead preferentially to one diastercoisomer 2. Force field calculations conducted on one pair of diastereoisomers 2c and 2'c predict that these isomers must exist in different conformations of similar energies. (t)H NMR data are in good agreement with these predictions. The dihydrofurans obtained by retro Diels-Alder reactions of 2 are easily transformed into optically pure 1,3-diols, precursors of R-(+)-alpha-lipoic acid and (-)-(1R,3R,5S)- 1,3-dimethyl -2,9-dioxabicyclo [3,3,1]nonane.

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收藏

页码：453 / 462

页数：10

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