Synthesis of optically-active benzylic amines; asymmetric reduction of ketoxime ethers with chiral oxazaborolidines

被引：38

作者：

Fontaine, E ^{[1
]}

Namane, C ^{[1
]}

Meneyrol, J ^{[1
]}

Geslin, M ^{[1
]}

Serva, L ^{[1
]}

Roussey, E ^{[1
]}

Tissandié, S ^{[1
]}

Maftouh, M ^{[1
]}

Roger, P ^{[1
]}

机构：

[1] Sanofi Synthelabo Rech, Rech Exploratoire, F-31036 Toulouse, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(01)00358-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation of novel optically active benzylic amines by the enantio selective reduction of phenone oximes using chiral oxazaborolidine is described. The choice of the chiral 1,2-amino alcohol (S)-diphenylvalinol as chiral inducer and that of the benzyl group for the O-oxime substituent is explained. 23 primary amines are obtained, with high enantio selectivity (e.e. = 98%), good yield (74%) on preparative scale. A mechanistic explanation is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2185 / 2189

页数：5

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