A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: Its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition

被引:434
作者
Hayashi, T [1 ]
Ueyama, K [1 ]
Tokunaga, N [1 ]
Yoshida, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja037367z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to α,β-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity. Copyright © 2003 American Chemical Society.
引用
收藏
页码:11508 / 11509
页数:2
相关论文
共 36 条
  • [1] Abel E.W., 1995, COMPREHENSIVE ORGANO
  • [2] Amengual R, 2002, SYNLETT, P1791
  • [3] AYLETT BJ, 1995, DICT ORGANOMETALLIC, V2
  • [4] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds
    Fagnou, K
    Lautens, M
    [J]. CHEMICAL REVIEWS, 2003, 103 (01) : 169 - 196
  • [5] Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates
    Hayashi, T
    Takahashi, M
    Takaya, Y
    Ogasawara, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) : 5052 - 5058
  • [6] Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes
    Hayashi, T
    Senda, T
    Ogasawara, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (43) : 10716 - 10717
  • [7] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES
    HAYASHI, T
    KONISHI, M
    KOBORI, Y
    KUMADA, M
    HIGUCHI, T
    HIROTSU, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) : 158 - 163
  • [8] Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates
    Hayashi, T
    Senda, T
    Takaya, Y
    Ogasawara, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) : 11591 - 11592
  • [9] Hayashi T, 2001, SYNLETT, P879
  • [10] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions
    Hayashi, T
    Yamasaki, K
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2829 - 2844