Enantioselective organocatalytic tandem Michael-aldol reactions: One-pot synthesis of chiral thiochromenes

被引:374
作者
Wang, Wei [1 ]
Li, Hao [1 ]
Wang, Jian [1 ]
Zu, Liansuo [1 ]
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
关键词
D O I
10.1021/ja063328m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly enantioselective (S) diphenylpyrrolinol silyl ether promoted tandem Michael-aldol reaction of α,β-unsaturated aldehydes with 2-mercaptobenzaldehydes has been developed. The method affords one-pot access to chiral and synthetically useful thiochromenes in high yields and high enantioselectivities from readily available compounds. Copyright © 2006 American Chemical Society.
引用
收藏
页码:10354 / 10355
页数:2
相关论文
共 45 条
  • [1] Ali A, 2001, EUR J ORG CHEM, V2001, P529, DOI 10.1002/1099-0690(200102)2001:3<529::AID-EJOC529>3.0.CO
  • [2] 2-B
  • [3] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
    Austin, JF
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
  • [4] A practical access to acyl radicals from acyl hydrazides
    Bath, S
    Laso, NM
    Lopez-Ruiz, H
    Quiclet-Sire, B
    Zard, SZ
    [J]. CHEMICAL COMMUNICATIONS, 2003, (02) : 204 - 205
  • [5] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [6] Berlin K. D., 2003, U.S. Patent, Patent No. [6,586,460, 6586460]
  • [7] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
    Betancort, JM
    Sakthivel, K
    Thayumanavan, R
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
  • [8] The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase
    Brown, MJ
    Carter, PS
    Fenwick, AE
    Fosberry, AP
    Hamprecht, DW
    Hibbs, MJ
    Jarvest, RL
    Mensah, L
    Milner, PH
    O'Hanlon, PJ
    Pope, AJ
    Richardson, CM
    West, A
    Witty, DR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (21) : 3171 - 3174
  • [9] Direct amino acid catalyzed asymmetric synthesis of polyketide sugars
    Casas, J
    Engqvist, M
    Ibrahem, I
    Kaynak, B
    Córdova, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) : 1343 - 1345
  • [10] In the golden age of organocatalysis
    Dalko, PI
    Moisan, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175