Direct Asymmetric Aldol Reaction Co-catalyzed by Amphiphilic Prolinamide Phenol and Lewis Acidic Metal on Water

被引：10
|
作者：
Zhang, Tao [1 ]
Zhang, Yunxiao [1 ]
Li, Zaichun [1 ]
Song, Zhongtai [1 ]
Liu, Hao [1 ]
Tao, Jingchao [1 ]
机构：
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2013年 / 31卷 / 02期
关键词：
Aldol reaction; amphiphilic prolinamide; Lewis acidic metal; co-cayalyst; asymmetric catalysis; ORGANIC-SYNTHESIS; AQUEOUS-MEDIA; ORGANOCATALYSTS; KETONES; CONDENSATION; ALDEHYDES; PROGRESS; ZINC;
D O I：
10.1002/cjoc.201201017
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An approach based on combinations of various water compatible Lewis acids and lipophilic group containing amphiphilic prolinamide co-catalysts has been evaluated for the direct asymmetric Aldol reaction. From the broad screening of chloride salts from alkali metal to transition metal, LiCl, ZnCl2 and SnCl2 lead to the highest stereoselectivities. The optimized catalytic conditions (10 mol% prolinamide with 10 mol% MCl2 or 20 mol% LiCl at room temperature on water) gave anti-products with improved enantioselectivities (up to 99% ee) compared to the moderately stereoselective procedure based on prolinamide activation only.
引用
收藏
页码：247 / 255
页数：9
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