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 50 条

[21] Enantioselective synthesis of bis-α-amino acid esters via asymmetric phase-transfer catalysis.
Lygo, B
Crosby, J
Peterson, JA
TETRAHEDRON LETTERS, 1999, 40 (07) : 1385 - 1388
[22] A Highly Enantioselective Overman Rearrangement through Asymmetric Counteranion-Directed Palladium Catalysis
Jiang, Gaoxi
Halder, Rajkumar
Fang, Yewen
List, Benjamin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (41) : 9752 - 9755
[23] Kinetics of the catalysed polymerisation of styrene part I Experimental methods and some general features of stannic chloride catalysis.
Williams, G
JOURNAL OF THE CHEMICAL SOCIETY, 1938, : 246 - 253
[24] Desymmetrization of meso [3.2.1]oxabicyclic systems using metal-catalysed asymmetric intramolecular C-H insertion
Zhang, Xiaomei
Li, Zhengning
Chu, John C. K.
Chiu, Pauline
TETRAHEDRON LETTERS, 2011, 52 (50) : 6763 - 6766
[25] Optically active nitrogen ligands in asymmetric catalysis. Effect of nitrogen substitution on the enantioselective hydride transfer reduction of acetophenone
Touchard, F
Bernard, M
Fache, F
Delbecq, F
Guiral, V
Sautet, P
Lemaire, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 567 (1-2) : 133 - 136
[26] Asymmetric catalysis in a micro reactor -: Ce, Yb and Lu catalysed enantioselective addition of trimethylsilyl cyanide to benzaldehyde
Jönsson, CI
Lundgren, S
Haswell, SJ
Moberg, C
TETRAHEDRON, 2004, 60 (46) : 10515 - 10520
[27] Chiral counteranions in enantioselective copper-catalyzed olefin aziridination: The importance of ion interactions in metal catalysis.
Arndtsen, BA
Llewellyn, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U895 - U896
[28] Enantioselective catalysis. Part 133: Conformational analysis of amides of 9-amino(9-deoxy)epicinchonine
Brunner, H
Schmidt, P
Prommesberger, M
TETRAHEDRON-ASYMMETRY, 2000, 11 (07) : 1501 - 1512
[29] Kinetics of the catalysed polymerisation of styrene Part III On the mechanism of metal chloride catalysis
Williams, G
JOURNAL OF THE CHEMICAL SOCIETY, 1940, : 775 - 784
[30] Kinetics and mechanism of metal ion catalysis. Part III. Osmium(VIII) catalysed oxidation of m-hydroxybenzaldehyde by Fe(CN)63− in alkaline medium
Satya P.S. Mehta
Geeta Tewary
Transition Metal Chemistry, 2002, 27 : 751 - 755

← 1 2 3 4 5 →