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

页码：2177 / 2187

页数：11

共 32 条

[21]

KLOSE R, 2002, S KEMATIN

[22]

KREUTZER G, 2003, THESIS U REGENSBURG

[23] COPPER(II) COMPLEXES WITH OPTICALLY-ACTIVE DIAMINES .1. SYNTHESIS AND PROPERTIES OF COPPER(II) COMPLEXES WITH N-BENZYL AND N-METHYL DERIVATIVES OF 1,2-DIAMINOPROPANE [J].