BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids

被引:172
作者
Reetz, MT [1 ]
Moulin, D [1 ]
Gosberg, A [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/ol010219y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] BINOL-based diphosphonites having achiral backbones are useful ligands in the Rh-catalyzed conjugate addition of arylboronic acids to alpha,beta -unsaturated carbonyl compounds. The nature of the achiral backbone determines the direction and degree of enantioselectivity, with er values of up to 99.5:0.5 possible.
引用
收藏
页码:4083 / 4085
页数:3
相关论文
共 12 条
  • [1] 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
  • [2] 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
  • [3] Hayashi T, 2001, SYNLETT, P879
  • [4] Novel synthesis of α-amino acids via catalysis in air and water
    Huang, TS
    Li, CJ
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 2037 - 2039
  • [5] A conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by 2β-CD-[Rh(OH)(cod)]2 or [RhCl(cod)]2 in a single aqueous medium
    Itooka, R
    Iguchi, Y
    Miyaura, N
    [J]. CHEMISTRY LETTERS, 2001, (07) : 722 - 723
  • [6] Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones
    Kuriyama, M
    Tomioka, K
    [J]. TETRAHEDRON LETTERS, 2001, 42 (05) : 921 - 923
  • [7] Strategies for the development of enantioselective catalysts
    Reetz, MT
    [J]. PURE AND APPLIED CHEMISTRY, 1999, 71 (08) : 1503 - 1509
  • [8] Diphosphonites as highly efficient ligands for enantioselective rhodium-catalyzed hydrogenation
    Reetz, MT
    Gosberg, A
    Goddard, R
    Kyung, SH
    [J]. CHEMICAL COMMUNICATIONS, 1998, (19) : 2077 - 2078
  • [9] REETZ MT, 1998, Patent No. 198402791
  • [10] Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap
    Sakuma, S
    Sakai, M
    Itooka, R
    Miyaura, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 5951 - 5955