A catalytic asymmetric method for the synthesis of γ-unsaturated β-amino acid derivatives

被引:87
作者
Lurain, AE [1 ]
Walsh, PJ [1 ]
机构
[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ja035213d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic enantioselective synthesis of beta-amino acid derivatives is an area of intense interest, due to the importance of these compounds as components in pharmaceutical agents and peptidomimetics. In this report, we present the first catalytic enantioselective method for the synthesis of gamma-unsaturated beta-amino acids and their corresponding 1,3-amino alcohol derivatives. This methodology takes advantage of a highly enantioselective vinylzinc addition to an aldehyde to set chirality. The resulting allylic alcohols are then transformed into the corresponding allylic amines via Overman's [3,3]-sigmatropic imidate rearrangement, and subsequent one-pot deprotection-oxidation of a pendant oxygen leads to the gamma-unsaturated beta-amino acid derivatives of high enantiopurity.
引用
收藏
页码:10677 / 10683
页数:7
相关论文
共 87 条
  • [1] ACHIWA K, 1978, TETRAHEDRON LETT, P1119
  • [2] Andersson MA, 2002, ANGEW CHEM INT EDIT, V41, P472, DOI 10.1002/1521-3773(20020201)41:3<472::AID-ANIE472>3.0.CO
  • [3] 2-7
  • [4] [Anonymous], 1994, Aldrichimica Acta
  • [5] The Sharpless asymmetric aminohydroxylation
    Bodkin, JA
    McLeod, MD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24): : 2733 - 2746
  • [6] N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins
    Bruncko, M
    Schlingloff, G
    Sharpless, KB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1483 - 1486
  • [7] Conjugate addition of hydroxylamino derivatives to alkylidene malonates in the presence of chiral Lewis acids
    Cardillo, G
    Gentilucci, L
    Gianotti, M
    Kim, H
    Perciaccante, R
    Tolomelli, A
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (17) : 2395 - 2398
  • [8] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids
    Cardillo, G
    Tomasini, C
    [J]. CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) : 117 - &
  • [9] CHAUDHARY SK, 1979, TETRAHEDRON LETT, P95
  • [10] A general, highly enantioselective method for the synthesis of D and L α-amino acids and allylic amines
    Chen, YK
    Lurain, AE
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (41) : 12225 - 12231