ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES CATALYZED BY CHIRAL NI(II) AMINOALCOHOL COMPLEXES

被引：89
|
作者：
DEVRIES, AHM [1 ]
JANSEN, JFGA [1 ]
FERINGA, BL [1 ]
机构：
[1] UNIV GRONINGEN,CTR CATALYSIS & SYNTH,DEPT ORGAN & MOLEC INORGAN CHEM,9747 AG GRONINGEN,NETHERLANDS
来源：
TETRAHEDRON | 1994年 / 50卷 / 15期
关键词：
D O I：
10.1016/S0040-4020(01)89380-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Conjugate addition of diethylzinc to chalcones is catalysed by complexes prepared in situ from Ni(acac)(2) and cis-exo-N,N-dialkyl-3-aminoisoborneols or (+)-cis-endo-N,N-dimethyl-3-aminoborneol ((+)- DAB) (13b). The products are obtained with enantioselectivities up to 84 %. When scalemic (-)-cis-exo-N,N-dimethyl-3-aminoisoborneol ((-)-DAIB) (3c) was employed in the reaction a positive nonlinear relationship was found. Several factors which govern catalyst activity and enantioselectivity have been investigated.
引用
收藏
页码：4479 / 4491
页数：13
相关论文
共 50 条
  • [1] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC USING NI(II) DAIB COMPLEXES
    JANSEN, JFGA
    FERINGA, BL
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (05) : 581 - 582
  • [2] Catalytic enantioselective conjugate addition of diethylzinc to chalcones using chiral amino alcohol-nickel complexes
    Wakimoto, I
    Tomioka, Y
    Kawanami, Y
    [J]. TETRAHEDRON, 2002, 58 (40) : 8095 - 8097
  • [3] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ARYLALDEHYDES CATALYZED BY CHIRAL COBALT(II) AND PALLADIUM(II) COMPLEXES
    OGUNI, N
    OMI, T
    YAMAMOTO, Y
    NAKAMURA, A
    [J]. CHEMISTRY LETTERS, 1983, (06) : 841 - 842
  • [4] The enantioselective diethylzinc addition to imines catalyzed by chiral Cu(II)-oxazoline complexes
    Li, X
    Cun, LF
    Gong, LZ
    Mi, AQ
    Jiang, YZ
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3819 - 3821
  • [5] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO ENONES USING CHIRAL BETA-AMINOALCOHOL AS CHIRAL CATALYST OR LIGAND
    SOAI, K
    OKUDO, M
    OKAMOTO, M
    [J]. TETRAHEDRON LETTERS, 1991, 32 (01) : 95 - 96
  • [6] Highly enantioselective conjugate addition of diethylzinc to substituted chalcones catalyzed by Cu(II) complexes of a tridentate P,N,O ligand
    Biradar, Deepak Baburao
    Gau, Han-Mou
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (06) : 733 - 738
  • [7] Enantioselective Conjugate Addition of Diethylzinc to Chalcone Catalyzed by Ni(acac)2 and Chiral β-Amino Alcohols
    王恒山
    达朝山
    辛卓群
    粟武
    肖亦男
    刘大学
    王锐
    [J]. Chinese Journal of Chemistry, 2003, (08) : 1105 - 1107
  • [8] Enantioselective conjugate addition of diethylzinc to chalcone catalyzed by Ni(acac)2 and chiral β-amino alcohols
    Wang, HS
    Da, CS
    Xin, ZQ
    Su, W
    Xiao, YN
    Liu, DX
    Wang, R
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (08) : 1105 - 1107
  • [9] Enantioselective conjugate addition of diethylzinc to cyclohexenone catalyzed by a chiral aminophosphine-copper(II) triflate
    Mori, T
    Kosaka, K
    Nakagawa, Y
    Nagaoka, Y
    Tomioka, K
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (18) : 3175 - 3178
  • [10] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONE CATALYZED BY CHIRAL TRICARBONYL(ARENE)CHROMIUM NICKEL (II)
    UEMURA, M
    MIYAKE, R
    NAKAYAMA, K
    HAYASHI, Y
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (06) : 713 - 714
12345