Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

被引：55

作者：

Ostendorf, M ^{[1
]}

Romagnoli, R ^{[1
]}

Pereiro, IC ^{[1
]}

Roos, EC ^{[1
]}

Moolenaar, MJ ^{[1
]}

Speckamp, WN ^{[1
]}

Hiemstra, H ^{[1
]}

机构：

[1] UNIV AMSTERDAM,AMSTERDAM INST MOL STUDIES,ORGAN CHEM LAB,NL-1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(97)00154-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led 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 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

引用

页码：1773 / 1789

页数：17

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