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

页码：5777 / 5781

页数：5

共 40 条

[1] Asymmetric conjugate addition of ketones to β-nitrostyrenes by means of 1,2-amino-alcohol-derived prolinamides as bifunctional catalysts
Almasi, Diana
Alonso, Diego A.
Gomez-Bengoa, Enrique
Nagel, Yvonne
Najera, Carmen
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (14) : 2328 - 2343
[2] Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine
Alza, Esther
Cambeiro, Xacobe C.
Jimeno, Ciril
Pericas, Miquel A.
[J]. ORGANIC LETTERS, 2007, 9 (19) : 3717 - 3720
[3] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[4] Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins
Cao, Chun-Li
Ye, Meng-Chun
Sun, Xiu-Li
Tang, Yong
[J]. ORGANIC LETTERS, 2006, 8 (14) : 2901 - 2904
[5] Self-assembly of organocatalysts: Fine-tuning organocatalytic reactions
Clarke, Matthew L.
Fuentes, Jose A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) : 930 - 933
[6] Enantioselective nitro-Michael reactions catalyzed by short peptides on water
Freund, Matthias
Schenker, Sebastian
Tsogoeva, Svetlana B.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) : 4279 - 4284
[7] Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid
Gu, Qing
Guo, Xing-Tao
Wu, Xin-Yan
[J]. TETRAHEDRON, 2009, 65 (27) : 5265 - 5270
[8] Asymmetric Michael Addition of γ,γ-Disubstituted α,β-Unsaturated Aldehydes to Nitroolefins via Dienamine Catalysis
Han, Bo
Xiao, You-Cai
He, Zhao-Quan
Chen, Ying-Chun
[J]. ORGANIC LETTERS, 2009, 11 (20) : 4660 - 4663
[9] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst
Huang, Hongbing
Jacobsen, Eric N.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7170 - 7171
[10] A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions
Ishii, T
Fujioka, S
Sekiguchi, Y
Kotsuki, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9558 - 9559

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