Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins

被引:25
作者
Kumar, Togapur Pavan [1 ]
Balaji, Sirinyam Venugopal [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
ENANTIOSELECTIVE CONJUGATE ADDITION; BETA-NITROSTYRENES; ALDOL REACTIONS; NITRO-MICHAEL; BIFUNCTIONAL ORGANOCATALYSTS; EFFICIENT ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; CYCLIC-KETONES; IONIC LIQUIDS; ALDEHYDES;
D O I
10.1016/j.tetasy.2014.02.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:473 / 477
页数:5
相关论文
共 97 条
[81]   Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts [J].
Tsogoeva, SB ;
Wei, SW .
CHEMICAL COMMUNICATIONS, 2006, (13) :1451-1453
[82]   Asymmetric organocatalysis with novel chiral thiourea derivatives: Bifunctional catalysts for the Strecker and nitro-Michael reactions [J].
Tsogoeva, SB ;
Yalalov, DA ;
Hateley, MJ ;
Weckbecker, C ;
Huthmacher, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (23) :4995-5000
[83]   Recent advances in asymmetric organocatalytic 1,4-conjugate additions [J].
Tsogoeva, Svetlana B. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (11) :1701-1716
[84]   Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts [J].
Vakulya, B ;
Varga, S ;
Csámpai, A ;
Soós, T .
ORGANIC LETTERS, 2005, 7 (10) :1967-1969
[85]   Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins [J].
Vishnumaya ;
Singh, Vinod K. .
ORGANIC LETTERS, 2007, 9 (06) :1117-1119
[86]   Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones [J].
Wang, J ;
Li, H ;
Zu, LS ;
Wang, W .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (4-5) :425-428
[87]   Enantio- and diastereoselective Michael addition reactions of unmodified aldehydes and ketones with nitroolefins catalyzed by a pyrrolidine sulfonamide [J].
Wang, Jian ;
Li, Hao ;
Lou, Bihshow ;
Zu, Liansuo ;
Guo, Hua ;
Wang, Wei .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) :4321-4332
[88]   Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes [J].
Wang, W ;
Wang, J ;
Li, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1369-1371
[89]   New highly enantioselective thiourea-based bifunctional organocatalysts for nitro-Michael addition reactions [J].
Wei, Shengwei ;
Yalalov, Denis A. ;
Tsogoeva, Svetlana B. ;
Schmatz, Stefan .
CATALYSIS TODAY, 2007, 121 (1-2) :151-157
[90]   Simple Chiral Pyrrolidine-Pyridine-Based Catalysts for Highly Enantioselective Michael Addition to Nitro Olefins [J].
Xu, Da-Zhen ;
Shi, Sen ;
Wang, Yongmei .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (28) :4848-4853