Asymmetric chemo- and regiospecific addition of organozinc reagents to Baylis-Hillman derived allylic electrophiles

被引:48
作者
Börner, C
Gimeno, J
Gladiali, S
Goldsmith, PJ
Ramazzotti, D
Woodward, S
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain
[3] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
D O I
10.1039/b006943o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The copper-catalysed S(N)2' addition of ZnR2 to allylic (Z)-ArCH=C(CH2X)(CO2Et) (X = Br, Cl, OSO2Me) fashions only ArCH(R)C(=CH2)(CO2Et); use of a chiral ligand gives up to 64% ee for this demanding reaction.
引用
收藏
页码:2433 / 2434
页数:2
相关论文
共 19 条
  • [1] Diphenylpropionic acids as new AT(1) selective angiotensin II antagonists
    Almansa, C
    Gomez, LA
    Cavalcanti, FL
    deArriba, AF
    Rodriguez, R
    Carceller, E
    GarciaRafanell, J
    Forn, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) : 2197 - 2206
  • [2] NECIC ACID SYNTHONS .2. REGIOSELECTIVITY IN THE REACTIONS OF (Z)-2-BROMOMETHYL-2-ALKENOATE ESTERS WITH SELECTED CARBON NUCLEOPHILES
    AMEER, F
    DREWES, SE
    EMSLIE, ND
    KAYE, PT
    MANN, RL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10): : 2293 - 2295
  • [3] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
    Basavaiah, D
    Rao, PD
    Hyma, RS
    [J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
  • [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] Dübner F, 1999, ANGEW CHEM INT EDIT, V38, P379, DOI 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO
  • [6] 2-Y
  • [7] DUBNER F, 2000, CHEM ABST 222063, V132
  • [8] Regio- and enantio-selective allylic alkylation catalysed by a chiral monophosphine-palladium complex
    Hayashi, T
    Kawatsura, M
    Uozumi, Y
    [J]. CHEMICAL COMMUNICATIONS, 1997, (06) : 561 - 562
  • [9] First enantioselective alkylations of monosubstituted allylic acetates catalyzed by chiral iridium complexes
    Janssen, JP
    Helmchen, G
    [J]. TETRAHEDRON LETTERS, 1997, 38 (46) : 8025 - 8026
  • [10] TETRAKIS(ACETONITRILE)COPPER(1+) HEXAFLUOROPHOSPHATE(1-) - CU2O+2HPF6CH3CN-]2[CU(CH3CN)4][PF6]+H2O
    KUBAS, GJ
    [J]. INORGANIC SYNTHESES, 1990, 28 : 68 - 70