ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES - SYNTHESES AND APPLICATION OF 2 CHIRAL BETA-AMINO ALCOHOLS FROM (S)-2-INDOLINE CARBOXYLIC-ACID

被引：63

作者：

MARTENS, J

DAUELSBERG, C

BEHNEN, W

WALLBAUM, S

机构：

[1] Fachbereich Chemie, Universität Oldenburg Ammerländer, D-2900 Oldenburg i.O.

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(00)80271-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of (S)-alpha,alpha-diphenyl-(indolin-2-yl)methanol 1 makes available the chiral oxazaborolidine 2 which is an excellent catalyst for borane reduction of prochiral ketones to chiral secondary alcohols, e.g. acetophenone, in high optical purity The new chiral auxiliary 1 is sythesized from (S)-2-indoline carboxylic acid in a two step procedure. (S)-(Indolin-2-yl)methanol 3 is converted to the oxazaborolidine 4 which served also as an enantioselective catalyst in the reduction of aromatic ketones with BH3.THF.

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页码：347 / 350

页数：4

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