Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

被引：28

作者：

Cao, Xiao-Yu ^{[1
,2
]}

Zheng, Jun-Cheng ^{[1
]}

Li, Yu-Xue ^{[1
]}

Shu, Zhen-Cao ^{[1
]}

Sun, Xiu-Li ^{[1
]}

Wang, Bi-Qin ^{[2
]}

Tang, Yong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610066, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 51期

基金：

中国国家自然科学基金;

关键词：

Pyrrolidine-urea; Bifunctional; Organocatalyst; Michael addition; Nitroalkene; DIRECT CONJUGATE ADDITION; AMINE-THIOUREA CATALYST; ENANTIOSELECTIVE MICHAEL; BICYCLIC SKELETONS; NITROOLEFINS; ALDEHYDES; EFFICIENT; CYCLOHEXANONE; CONSTRUCTION; DERIVATIVES;

D O I：

10.1016/j.tet.2010.10.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：9703 / 9707

页数：5

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