Synthesis of prolinal dithioacetals as catalysts for the highly stereoselective Michael addition of ketones and aldehydes to β-nitrostyrenes

被引:34
作者
Mandal, Tanmay [1 ]
Zhao, Cong-Gul [1 ]
机构
[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA
关键词
asymmetric; dithioacetals; beta-nitrostyrene; N-Boc-prolinal; proline; enantioselective; diastereoselective;
D O I
10.1016/j.tetlet.2007.06.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic highly enantioselective (up to > 99% ee) and diastereoselective (up to 99% de) direct Michael addition of ketones and aldehydes to beta-nitrostyrenes have been achieved with readily accessible and highly tunable prolinal dithioacetal catalysts. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5803 / 5806
页数:4
相关论文
共 48 条
  • [1] 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
  • [2] 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
  • [3] [Anonymous], ACC CHEM RES
  • [4] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [5] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [6] 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
  • [7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [8] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
  • [9] 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
  • [10] Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts
    Cao, Yi-Ju
    Lai, Yuan-Yuan
    Wang, Xiang
    Li, Yong-Han
    Xiao, Wen-Jing
    [J]. TETRAHEDRON LETTERS, 2007, 48 (01) : 21 - 24