Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc

被引:120
作者
Alexakis, A [1 ]
Polet, D [1 ]
Rosset, S [1 ]
March, S [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
关键词
D O I
10.1021/jo049359m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphoramidite ligands, based on ortho-substituted biphenols and a chiral amine, induce high enantioselectivities (ee's up to 99%) in the copper-catalyzed conjugate addition of dialkylzinc reagents to a variety of Michael acceptors. Particularly, the best reported ee's were obtained for acyclic nitroolefins.
引用
收藏
页码:5660 / 5667
页数:8
相关论文
共 28 条
  • [11] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition
    Feringa, BL
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 346 - 353
  • [12] Palladium-catalyzed synthesis of tetraethynyl and tetraethenyl biphenyls: Elongated tetrahedral tectons
    GomezLor, B
    Echavarren, AM
    Santos, A
    [J]. TETRAHEDRON LETTERS, 1997, 38 (30) : 5347 - 5350
  • [13] THE REACTIONS OF AN ORTHO-QUINONE MONOIMIDE WITH SOME PHENOLS
    HEINE, HW
    CIACCIO, JA
    CARSON, KG
    TAYLOR, CM
    WILLIAMS, EA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4039 - 4043
  • [14] Hu XQ, 1999, ANGEW CHEM INT EDIT, V38, P3518, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO
  • [15] 2-P
  • [16] New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations
    Hua, ZH
    Vassar, VC
    Choi, H
    Ojima, I
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5411 - 5416
  • [17] REACTIONS OF ALKYL-LITHIUM COMPOUNDS WITH ARYL HALIDES
    HUDDLE, PA
    PEROLD, GW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12): : 2617 - 2625
  • [18] Krause N, 2001, SYNTHESIS-STUTTGART, P171
  • [19] MONETA W, 1988, B SOC CHIM FR, P995
  • [20] QIU W, 2000, Patent No. 6077979