A high yielding route to substituted piperidines via the aza-Diels-Alder reaction

被引:19
作者
Bailey, PD
Smith, PD
Pederson, F
Clegg, W
Rosair, GM
Teat, SJ
机构
[1] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland
[2] CLRC, Daresbury Lab, Warrington WA4 4AD, Cheshire, England
[3] Newcastle Univ, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
alkaloids; Diels-Alder reaction; piperidines;
D O I
10.1016/S0040-4039(01)02148-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The imine Ph2CHN-CHCO2Et, generated from benzhydrylamine and ethyl glyoxylate, is an excellent dienophile in aza-Diels-Alder reactions, giving diastereomerically pure cycloadducts in high yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1067 / 1070
页数:4
相关论文
共 14 条
  • [1] DIASTEREOSELECTIVE AZA-DIELS-ALDER REACTION - USE OF 1-PHENYLETHYLIMINE OF ALKYL GLYOXYLATE FOR SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS
    ABRAHAM, H
    STELLA, L
    [J]. TETRAHEDRON, 1992, 48 (44) : 9707 - 9718
  • [2] Asymmetric routes to substituted piperidines
    Bailey, PD
    Millwood, PA
    Smith, PD
    [J]. CHEMICAL COMMUNICATIONS, 1998, (06) : 633 - 640
  • [3] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION
    BAILEY, PD
    BROWN, GR
    KORBER, F
    REED, A
    WILSON, RD
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1263 - 1282
  • [4] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION OF IMINES WITH DIENES
    BAILEY, PD
    WILSON, RD
    BROWN, GR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05): : 1337 - 1340
  • [5] STEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING AZA-DIELS-ALDER REACTIONS
    BAILEY, PD
    WILSON, RD
    BROWN, GR
    [J]. TETRAHEDRON LETTERS, 1989, 30 (48) : 6781 - 6784
  • [6] BAILEY PD, 1994, CHEM COMMUN, P2543
  • [7] Boger D. L., 1987, HETERO DIELS ALDER M
  • [8] *BRUK AXS, 1994, XSCANS DAT COLL RED
  • [9] Recent developments in imino Diels-Alder reactions
    Buonora, P
    Olsen, JC
    Oh, T
    [J]. TETRAHEDRON, 2001, 57 (29) : 6099 - 6138
  • [10] A new high-flux chemical and materials crystallography station at the SRS Daresbury .1. Design, construction and test results
    Cernik, RJ
    Clegg, W
    Catlow, CRA
    BushnellWye, G
    Flaherty, JV
    Greaves, GN
    Burrows, I
    Taylor, DJ
    Teat, SJ
    Hamichi, M
    [J]. JOURNAL OF SYNCHROTRON RADIATION, 1997, 4 : 279 - 286