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

页码：782 / 787

页数：6

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