OXAZABOROLIDINE CATALYZED ENANTIOSELECTIVE REDUCTIONS OF CYCLIC MESO-IMIDES

被引：39

作者：

ROMAGNOLI, R

ROOS, EC

HIEMSTRA, H

MOOLENAAR, MJ

SPECKAMP, WN

KAPTEIN, B

SCHOEMAKER, HE

机构：

[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,1018 WS AMSTERDAM,NETHERLANDS

[2] DSM RES BV,DEPT BIOORGAN CHEM,6160 MD GELEEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)79972-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.

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页码：1087 / 1090

页数：4

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