Catalytic enantioselective Conia-ene reaction

被引:178
作者
Corkey, BK [1 ]
Toste, FD [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja055059q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantioselective intramolecular Conia-ene reaction of β-dicarbonyl compounds and alkynes to afford methylene cyclopentanes is described. The reaction employs a DTBMSegphos-Pd(II)/Yb(III) dual catalyst system that allows for the asymmetric synthesis of all-carbon quaternary centers and generates a product containing an alkene that can be further manipulated. Copyright © 2005 American Chemical Society.
引用
收藏
页码:17168 / 17169
页数:2
相关论文
共 34 条
  • [1] FORMATION OF CYCLOPENTANES FROM DELTA-ETHYLENE MALONATES BY CATALYSIS IN PALLADIUM(0) - STEREOCHEMISTRY AND MECHANISM
    BALME, G
    BOUYSSI, D
    FAURE, R
    GORE, J
    VANHEMELRYCK, B
    [J]. TETRAHEDRON, 1992, 48 (19) : 3891 - 3902
  • [2] Organocatalytic enantioselective conjugate addition to alkynones
    Bella, M
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5672 - 5673
  • [3] Intramolecular carbocupration reaction of unactivated alkynes bearing a stabilized nucleophile: Application to the synthesis of iridoid monoterpenes.
    Bouyssi, D
    Monteiro, N
    Balme, G
    [J]. TETRAHEDRON LETTERS, 1999, 40 (07) : 1297 - 1300
  • [4] A theoretical and structural investigation of thiocarbon anions
    Chen, ZF
    Sutton, LR
    Moran, D
    Hirsch, A
    Thiel, W
    Schleyer, PV
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) : 8808 - 8814
  • [5] Catalytic asymmetric vinylation of ketone enolates
    Chieffi, A
    Kamikawa, K
    Åhman, J
    Fox, JM
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2001, 3 (12) : 1897 - 1900
  • [6] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions
    Christoffers, J
    Baro, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) : 1688 - 1690
  • [7] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
  • [8] 2-V
  • [9] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
  • [10] 2-V