A highly efficient and stereospecific borane reduction of spiro[4.4]nonane-1,6-dione catalyzed by a chiral oxazaborolidine

被引：8

作者：

Lin, CW

Lin, CC

Li, YM

Chan, ASC ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, Dept ABCT, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 22期

关键词：

asymmetric reactions; oxazaborolidine; reduction; spiro compounds;

D O I：

10.1016/S0040-4039(00)00606-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective and enantioselective reduction of racemic spiro[4.4]nonane-1,6-dione catalyzed by an oxazaborolidine reagent is described. The asymmetric reduction of the racemic spirodiketones resulted in enantiomerically pure spirodiols which are useful chiral auxiliaries and also key intermediates for the synthesis of other highly effective chiral ligands. The trans,trans- and cis,trans-spirodiols were prepared in high enantiopurity by employing chiral oxazaborolidine as the catalyst. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

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页码：4425 / 4429

页数：5

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