Highly Enantioselective Michael Addition of Acetone to Nitro Olefins Catalyzed by Chiral Bifunctional Primary Amine-Thiophosphoramide Catalyst

被引：33

作者：

Lu, Aidang ^{[1
]}

Liu, Tao ^{[1
]}

Wu, Ronghua ^{[1
]}

Wang, Youming ^{[1
]}

Zhou, Zhenghong ^{[1
]}

Wu, Guiping ^{[1
]}

Fang, Jianxin ^{[1
]}

Tang, Chuchi ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 30期

基金：

中国国家自然科学基金;

关键词：

Enantioselectivity; Michael addition; Nitro olefins; Chiral thiophosphoramide; ASYMMETRIC ORGANOCATALYSTS; CONJUGATE ADDITION; ALDOL REACTIONS; KETONES; THIOUREA; NITROOLEFINS; ALDEHYDES; NITROSTYRENES; WATER; ACID;

D O I：

10.1002/ejoc.201000945

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of bifunctional primary amine-thiophosphoramides were synthesized, which proven to be effective organocatalysts for the asymmetric Michael reaction of acetone to both aryl and alkyl nitro olefins in the presence of phenol as a protic additive. The corresponding adducts were obtained in excellent chemical yields (up to >99%) with excellent enantioselectivities (up to 97 % ee).

引用

收藏

页码：5777 / 5781

页数：5

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