Polystyrene supported benzoylthiourea-pyrrolidine organocatalyst for the enantioselective Michael addition

被引：11
|
作者：
Androvic, Ladislav [1 ]
Drabina, Pavel [1 ]
Svobodova, Marketa [1 ]
Sedlak, Milos [1 ]
机构：
[1] Univ Pardubice, Fac Chem Technol, Inst Organ Chem & Technol, Studentska 573, Pardubice 53210, Czech Republic
来源：
TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 16期
关键词：
RECYCLABLE CATALYST; COMPLEXES; HENRY; NITROOLEFINS; COPOLYMER; KETONES;
D O I：
10.1016/j.tetasy.2016.06.015
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Herein the preparation of a swellable pearl-like copolymer of styrene with anchored (S)-1-benzoyl-3-(pyrrolidine-2-ylmethyl)thiourea (20-600 mu m) and its application as a recyclable organocatalyst for the Michael addition of ketones to functionalized beta-nitrostyrenes is described. The rate of the reaction taking place in the matrix of the swellable polymeric catalyst was comparable with the reaction rate in homogeneous medium. The corresponding functionalized 4-nitroketones were formed quantitatively with the enantiomeric excesses up to 98% ee. After a fivefold recycling of the catalyst, no decrease in the yield was detected, but the enantioselectivity was slightly lowered (95 -> 88% ee). (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：782 / 787
页数：6
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