Copper-catalysed asymmetric 1,4-addition of organometallic reagents to 2-cyclohexenone using novel phosphine-phosphite ligands

被引:45
作者
Diéguez, M
Deerenberg, S
Pàmies, O
Claver, C
van Leeuwen, PWNM
Kamer, P
机构
[1] Univ Amsterdam, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
[2] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43005, Spain
关键词
D O I
10.1016/S0957-4166(00)00262-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of novel non-symmetrical phosphine-phosphite ligands 1-10 have been tested in the copper catalysed asymmetric addition of diethylzinc and triethylaluminium to 2-cyclohexenone. In all cases, excellent conversion and regioselectivities for the 1,4-product were found. Good enantiomeric excesses (up to 62%) were obtained when triethylaluminium was used as the alkylating reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3161 / 3166
页数:6
相关论文
共 30 条
  • [1] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL
    Alexakis, A
    Vastra, J
    Burton, J
    Benhaim, C
    Mangeney, P
    [J]. TETRAHEDRON LETTERS, 1998, 39 (43) : 7869 - 7872
  • [2] [Anonymous], ORGANOCOPPER REAGENT
  • [3] [Anonymous], TRANSITION METAL CAT
  • [4] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones
    Bennett, SMW
    Brown, SM
    Cunningham, A
    Dennis, MR
    Muxworthy, JP
    Oakley, MA
    Woodward, S
    [J]. TETRAHEDRON, 2000, 56 (18) : 2847 - 2855
  • [5] Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands
    Bennett, SMW
    Brown, SM
    Muxworthy, JP
    Woodward, S
    [J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1767 - 1770
  • [6] New chiral phosphine-phosphite ligands in the enantioselective rhodium-catalyzed hydroformylation of styrene
    Deerenberg, S
    Kamer, PCJ
    van Leeuwen, PWNM
    [J]. ORGANOMETALLICS, 2000, 19 (11) : 2065 - 2072
  • [7] DEERENBERG S, IN PRESS J ORG CHEM
  • [8] DEERENBERG S, UNPUB
  • [9] Enantioselective conjugate addition of dialkylzinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites
    deVries, AHM
    Meetsma, A
    Feringa, BL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20): : 2374 - 2376
  • [10] HALPERN J, 1985, ASYMMETRIC SYNTHESIS, V5