Asymmetric catalysis.: Part 153:: Metal-catalysed enantioselective α-ketol rearrangement

被引：56
|
作者：
Brunner, H
Kagan, HB
Kreutzer, G
机构：
[1] Univ Regensburg, Inst Anorgan Chem, D-93040 Regensburg, Germany
[2] Univ Paris 11, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 15期
关键词：
D O I：
10.1016/S0957-4166(03)00433-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Promoted by catalytic amounts of Ni complexes tertiary alpha-hydroxyketones 1a, 3a-5a undergo rearrangement, forming chiral isomers 1b, 3b-5b. The best enantioselection was obtained with the model system 1-benzoylcyclopentanol 4a/2-hydroxy-2-phenylcyclohexanone 4b. In a ligand screening 2-[4-(S)-tert-butyloxazolin-2-yl]pyridine gave the highest enantiomeric excess of 46% (S)-4b. The analogous isomerisation reactions of alpha-hydroxyimines 6a, 7a forming chiral alpha-aminoketones 6b, 7b were established. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2177 / 2187
页数：11
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