First enantioselective hydrogenation of a trifluoro-β-keloester with cinchona-modified platinum

被引：57

作者：

von Arx, M ^{[1
]}

Mallat, T ^{[1
]}

Baiker, A ^{[1
]}

机构：

[1] ETH Zentrum, Tech Chem Lab, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF CATALYSIS | 2000年 / 193卷 / 01期

关键词：

enantioselective hydrogenation; cinchonidine; platinum-alumina; trifluoromethyl ketones;

D O I：

10.1006/jcat.2000.2871

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of trifluoromethyl ketones possessing different functional groups were hydrogenated over Pt/Al2O3 modified by cinchonidine and O-methylcinchonidine. The highest enantiomeric epcess of 90% was achieved in the hydrogenation of ethyl 4,4,4-trifluoroacetoacetate. The remarkable variation of enantioselectivity in the synthesis of various alpha,alpha,alpha-trifluoromethyl alcohols is interpreted by electronic and steric effects. Future mechanistic studies have to clarify the unexpectedly big influence of acidic solvent and the special role of the (C9)-OH group in cinchonidine. (C) 2000 Academic Press.

引用

页码：161 / 164

页数：4

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