Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts

被引:149
作者
Fairlamb, IJS [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
atom economy; cyclization; enantioselectivity; palladium; rhodium; ruthenium;
D O I
10.1002/anie.200301699
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly functionalized carbo- and heterocycles can be prepared enantioselectively from simple enynes in transition-metal-catalyzed reactions. This versatile, atom-economic, and environmentally friendly approach has become a mainstay in natural product synthesis. The concise synthesis of (+)-pilocarpine is one example (see scheme). binap = 2,2′-bis- (diphenylphosphanyl)-1,1′-binaphthyl), cod = cyclooctacliene, RT = room temperature.
引用
收藏
页码:1048 / 1052
页数:5
相关论文
共 30 条
  • [1] AUBERT C, CHEM REV
  • [2] Cao P, 2000, ANGEW CHEM INT EDIT, V39, P4104, DOI 10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO
  • [3] 2-X
  • [4] Cao P., 2000, ANGEW CHEM, V112, P4270
  • [5] Enantioselective cyclization/hydrosilylation of 1,6-enynes catalyzed by a cationic rhodium bis(phosphine) complex
    Chakrapani, H
    Liu, C
    Widenhoefer, RA
    [J]. ORGANIC LETTERS, 2003, 5 (02) : 157 - 159
  • [6] Enantioselective cycloisomerization of 1,6-enynes catalyzed by chiral diphosphane-palladium complexes
    Goeke, A
    Sawamura, M
    Kuwano, R
    Ito, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (06): : 662 - 663
  • [7] Goeke A., 1996, ANGEW CHEM, V108, P686
  • [8] Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex
    Hatano, M
    Mikami, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) : 4704 - 4705
  • [9] Hatano M, 2001, ANGEW CHEM INT EDIT, V40, P249, DOI 10.1002/1521-3773(20010105)40:1<249::AID-ANIE249>3.0.CO
  • [10] 2-X