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

被引:24
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
  • [1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
    Alexakis, A
    Andrey, O
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
  • [2] 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
  • [3] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [4] 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
  • [5] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins
    Andrey, O
    Alexakis, A
    Tomassini, A
    Bernardinelli, G
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
  • [6] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
    Andrey, O
    Alexakis, A
    Bernardinelli, G
    [J]. ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
  • [7] [Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
  • [8] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results
    Ballini, R
    Bosica, G
    Fiorini, D
    Palmieri, A
    Petrini, M
    [J]. CHEMICAL REVIEWS, 2005, 105 (03) : 933 - 971
  • [9] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [10] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Tanaka, F
    Barbas, CF
    [J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521