Pyrrolidine-HOBt: an oxytriazole catalyst for the enantioselective Michael addition of cyclohexanone to nitroolefins in water

被引:13
|
作者
Kumar, Togapur Pavan [1 ,2 ]
Prasad, Sthanikam Siva [1 ,3 ]
Haribabu, Kothapalli [1 ]
Kumar, Veerjala Naveen [1 ]
Reddy, Cirandur Suresh [3 ]
机构
[1] Indian Inst Chem Technol, CSIR, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India
[2] Indian Inst Chem Technol, CSIR, Acad Sci & Innovat Res AcSIR, Hyderabad 500007, Andhra Pradesh, India
[3] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
关键词
ASYMMETRIC ALDOL REACTIONS; CONJUGATE ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; BETA-NITROSTYRENES; NITRO-MICHAEL; BIFUNCTIONAL ORGANOCATALYSTS; EFFICIENT ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; CYCLIC-KETONES; IONIC LIQUIDS;
D O I
10.1016/j.tetasy.2016.08.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new analogue of the proline derived organocatalyst 'pyrrolidine-HOBt' has been designed and synthesized from L-prolinol and hydroxybenzotriazole (HOBt) employing a simple reaction protocol. The catalyst was found to be effective in promoting the asymmetric Michael addition of cyclohexanone to nitroolefins using water as the reaction medium. The reaction products gamma-nitrocarbonyls are obtained in good yields and stereoselectivities. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1133 / 1138
页数:6
相关论文
共 50 条
  • [21] Highly enantioselective Michael addition of α,α-disubstituted aldehydes to nitroolefins
    Xing-Tao Guo
    Feng Sha
    Xin-Yan Wu
    Research on Chemical Intermediates, 2016, 42 : 6373 - 6380
  • [22] Ionic liquid-supported (ILS) (S)-pyrrolidine sulfonamide, an effective organocatalyst for the enantioselective Michael addition to nitroolefins
    Ni, Bukuo
    Zhang, Qianying
    Dhungana, Kritanjali
    Healdey, Allan D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [23] Highly Enantioselective Michael Addition of Ketones to Nitroolefins with a Pyrrolidine-Based Phthalimide as an Enamine-Type Organocatalyst
    Ban, Shu-rong
    Xie, Hong-yu
    Zhu, Xi-xia
    Li, Qing-shan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (32) : 6413 - 6417
  • [24] Asymmetric Michael addition of aldehydes to nitroolefins catalyzed by a pyrrolidine-pyrazole
    Kumar, Togapur Pavan
    TETRAHEDRON-ASYMMETRY, 2014, 25 (18-19) : 1286 - 1291
  • [25] A chiral amino-naphthalene-derived prolinamide catalyst for the enantioselective Michael addition of ketones to nitroolefins
    Yu, Chuanming
    Zhang, Ke
    Shi, Xiangjun
    JOURNAL OF CHEMICAL RESEARCH, 2012, (05) : 278 - 282
  • [26] An amphiphilic organic catalyst for the direct asymmetric Michael addition of cycloketone to nitroolefins in water
    Wei, Jianwei
    Guo, Wengang
    Zhang, Boyu
    Liu, Yan
    Du, Xin
    Li, Can
    CHINESE JOURNAL OF CATALYSIS, 2014, 35 (07) : 1008 - 1011
  • [27] A chiral benzoylthiourea-pyrrolidine catalyst for the highly enantioselective Michael addition of ketones to chalcones
    Ban, Shu-rong
    Zhu, Xi-xia
    Zhang, Zhi-ping
    Li, Qing-shan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (11) : 2517 - 2520
  • [28] A highly enantioselective organocatalyst for the Michael addition of cyclic ketones to nitroolefins
    Zhu, MK
    Cun, LF
    Mi, AQ
    Jiang, YZ
    Gong, LZ
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 491 - 493
  • [29] Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide, a Recyclable Organocatalyst for the Highly Enantioselective Michael Addition to Nitroolefins
    Ni, Bukuo
    Zhang, Qianying
    Dhungana, Kritanjali
    Headley, Allan D.
    ORGANIC LETTERS, 2009, 11 (04) : 1037 - 1040
  • [30] Enantioselective Michael addition of nitroolefins and cyclohexanones catalyzed by novel pyrrolidine-thiourea bifunctional catalysts with two chiral centers
    Cheng, Dongping
    Bao, Weiliang
    LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (05) : 342 - 345