Diastereoselective cycloadditions of new trifluoromethyl azomethine ylides derived from trifluorothioacetamides

被引:19
作者
Laduron, F [1 ]
Ates, C [1 ]
Viehe, HG [1 ]
机构
[1] UNIV CATHOLIQUE LOUVAIN, ORGAN CHEM LAB, B-1348 LOUVAIN, BELGIUM
关键词
D O I
10.1016/0040-4039(96)01185-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two methods of generation of new trifluoromethyl azomethine ylides are described: by heating N,N-dimethyl-bis(methylthio)-orthotrifluoroacetamide 2 or by deprotonation of trifluoromethyl thioamidium salts. Trapping by dipolarophiles leads to 2-trifluoromethyl pyrrolidines and pyrrolizidines with high diastereoselectivity. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:5515 / 5518
页数:4
相关论文
共 11 条
  • [1] BONNETT R, 1970, CHEM CARBON NITROGEN, pCH13
  • [2] Hetero-1,3-dipolar cycloadditions of dithiolane-isocyanate iminium methylides: A novel route to 1,3-oxazolidine- and thiazolidine-2-thiones
    Fishwick, CWG
    Foster, RJ
    Carr, RE
    [J]. TETRAHEDRON LETTERS, 1996, 37 (05) : 711 - 714
  • [3] Dithiolane-isocyanate imminium methylides: A rapid stereoselective entry into gamma-lactams
    Fishwick, CWG
    Foster, RJ
    Carr, RE
    [J]. TETRAHEDRON LETTERS, 1995, 36 (51) : 9409 - 9412
  • [4] CAPTO-DATIVE SUBSTITUENT EFFECTS .3. SYNTHESIS AND INTRA-MOLECULAR 1,3 CL,H DISPROPORTIONATION OF ETHYL 2,2-DICHLORO-2-(DIMETHYLAMINO)-ACETATE
    HUYS, F
    MERENYI, R
    JANOUSEK, Z
    STELLA, L
    VIEHE, HG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (08): : 615 - 616
  • [5] KANTLEHNER W, 1976, IMINIUM SALTS ORGA 2, P118
  • [6] NOVEL AND CONVENIENT ROUTES TO SUBSTITUTED PYRROLES AND IMIDAZOLES
    KATRITZKY, AR
    ZHU, L
    LANG, HY
    DENISKO, O
    WANG, ZQ
    [J]. TETRAHEDRON, 1995, 51 (48) : 13271 - 13276
  • [7] A NEW CONVENIENT METHOD TO OBTAIN PYRROLES FROM TERTIARY N-ALLYLTHIOAMIDES
    MAGEDOV, IV
    KORNIENKO, AV
    ZOTOVA, TO
    DROZD, VN
    [J]. TETRAHEDRON LETTERS, 1995, 36 (26) : 4619 - 4622
  • [8] TINANT B, IN PRESS
  • [9] ULRICH H, 1968, CHEM IMIDOYL HALIDES, pCH3
  • [10] VIEHE HG, 1989, NATO ADV SCI I C-MAT, V260, P1