Enantioselectively organocatalytic Michael addition of ketones to alkylidene malonates

被引:63
作者
Cao, Chun-Li [1 ]
Sun, Xiu-Li [1 ]
Zhou, Jiao-Long [1 ]
Tang, Yong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo070070p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An organocatalytic asymmetric Michael addition of ketones to alkylidene malonates has been developed. In the presence of 20 mol % of urea 1a or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1j, the reactions of ketones with alkylidene malonates afford the desired Michael adducts in moderate to good yields with good to high enantioselectivities under mild conditions.
引用
收藏
页码:4073 / 4076
页数:4
相关论文
共 66 条
  • [1] [Anonymous], 1992, CONJUGATED ADDITION
  • [2] 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
  • [3] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts
    Berkessel, A
    Cleemann, F
    Mukherjee, S
    Müller, TN
    Lex, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) : 807 - 811
  • [4] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [5] 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
  • [6] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
    Betancort, JM
    Barbas, CF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
  • [7] 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
  • [8] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
    Brandau, Sven
    Landa, Aitor
    Franzen, Johan
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
  • [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