Direct asymmetric aldol reaction co-catalyzed by L-proline and group 12 elements Lewis acids in the presence of water

被引：47
作者：
Penhoat, Mael [1 ]
Barbry, Didier
Rolando, Christian
机构：
[1] Univ Lille 1, CNRS, USR 3290, F-59655 Villeneuve Dascq, France
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 01期
关键词：
Aldol reaction; Dual activation; Lewis acids; Proline; ZINC; ORGANOCATALYSIS; MECHANISM; ENZYMES;
D O I：
10.1016/j.tetlet.2010.11.014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An approach based on combinations of various water compatible Lewis acids and L-proline co-catalysts has been evaluated for the direct asymmetric aldol reaction. From this broad screening, chloride salts from group 12 elements (ZnCl2, CdCl2, HgCl2) lead to the highest stereoselectivities. Optimized catalytic conditions (catalytic system: L-proline: 20%/ZnCl2: 10%; solvent mixture: DMSO/H2O, 8:2) gave anti aldol products with improved enantioselectivity (>99% ee) compared to a moderately stereoselective procedure based on proline activation only. (C) 2010 Elsevier Ltd. All rights reserved.
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收藏
页码：159 / 162
页数：4
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