Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL

被引:117
作者
Alexakis, A [1 ]
Vastra, J [1 ]
Burton, J [1 ]
Benhaim, C [1 ]
Mangeney, P [1 ]
机构
[1] Univ Paris 06, Dept Chim Organ, UMR 7611 CNRS, F-75252 Paris 05, France
关键词
D O I
10.1016/S0040-4039(98)01761-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric conjugate addition of diethyl zinc to cyclohexen-2-one, chalcone and benzalacetone was studied with 0.5% copper (II) triflate and 1% chiral phosphorus ligands derived from TADDOL. Among the several ligand tested, the cyclic phosphite obtained with 1S,2R phenylcyclohexanol gave up to 96% ee of conjugate adduct to cyclohexenone. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7869 / 7872
页数:4
相关论文
共 22 条
  • [1] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES
    AHN, KH
    KLASSEN, RB
    LIPPARD, SJ
    [J]. ORGANOMETALLICS, 1990, 9 (12) : 3178 - 3181
  • [2] Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands
    Alexakis, A
    Vastra, J
    Mangeney, P
    [J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7745 - 7748
  • [3] Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands
    Alexakis, A
    Vastra, J
    Burton, J
    Mangeney, P
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3193 - 3196
  • [4] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
    ALEXAKIS, A
    FRUTOS, J
    MANGENEY, P
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2427 - 2430
  • [5] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands
    Alexakis, A
    Burton, J
    Vastra, J
    Mangeney, P
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (24) : 3987 - 3990
  • [6] DAHINDEN R, 1995, ENCY REAGENTS ORGANI, P2167
  • [7] 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
  • [8] Diastereoselective synthesis of pyridyl substituted thiazolidin-4-ones. New ligands for the Cu(I) catalyzed asymmetric conjugate addition of diethylzinc to enones
    deVries, AHM
    Hof, RP
    Staal, D
    Kellogg, RM
    Feringa, BL
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1539 - 1543
  • [9] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents
    Feringa, BL
    Pineschi, M
    Arnold, LA
    Imbos, R
    de Vries, AHM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2620 - 2623
  • [10] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMAGNESIUM CUPRATES CONTROLLED BY A STOICHIOMETRIC AMOUNT OF CHIRAL PHOSPHINE
    KANAI, M
    TOMIOKA, K
    [J]. TETRAHEDRON LETTERS, 1995, 36 (24) : 4273 - 4274