Novel ruthenium-catalyzed cleavage of allyl protecting group in lactams

被引:34
作者
Alcaide, B [1 ]
Almendros, P
Alonso, JM
机构
[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
lactams; ruthenium; catalytic; allyl cleavage;
D O I
10.1016/j.tetlet.2003.09.165
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and general method of synthesis of NH-lactams via Grubbs' carbene promoted isomerization of the respective N-allyl lactams followed by RuCl3-catalyzed enamide cleavage has been developed. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8693 / 8695
页数:3
相关论文
共 20 条
  • [1] REGENTS AND SYNTHETIC METHODS .60. NEW STEREOCHEMICAL OUTCOMES IN THE CYCLOADDITION OF ACID HALIDES OR EQUIVALENTS TO CINNAMYLIDENEAMINES - A CONCISE NEW APPROACH TO 4-ACETOXYAZETIDIN-2-ONES
    AIZPURUA, JM
    COSSIO, FP
    LECEA, B
    PALOMO, C
    [J]. TETRAHEDRON LETTERS, 1986, 27 (36) : 4359 - 4362
  • [2] Non-metathetic behavior patterns of Grubbs' carbene
    Alcaide, B
    Almendros, P
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) : 1259 - 1262
  • [3] A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines
    Alcaide, B
    Almendros, P
    Alonso, JM
    Aly, MF
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3781 - 3784
  • [4] HEXACARBONYL DICOBALT COMPLEXED N-PROP-2-YNYL-2-AZETIDINONES - A NEW ENTRY TO N-UNSUBSTITUTED-BETA-LACTAMS THROUGH A NICHOLAS-TYPE REACTION
    ALCAIDE, B
    PEREZCASTELLS, J
    SANCHEZVIGO, B
    SIERRA, MA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (05) : 587 - 588
  • [5] Chemoselective radical cleavage of Cbz-protected nitrogen compounds
    Bennasar, ML
    Roca, T
    Padullés, A
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 569 - 572
  • [6] Cainelli G, 1997, SYNLETT, P923
  • [7] A new entry to N-unsubstituted β-lactams through a solid-phase approach
    Dasgupta, SK
    Banik, BK
    [J]. TETRAHEDRON LETTERS, 2002, 43 (51) : 9445 - 9447
  • [8] RECENT DEVELOPMENTS IN THE FIELD OF BETA-LACTAM ANTIBIOTICS
    DURCKHEIMER, W
    BLUMBACH, J
    LATTRELL, R
    SCHEUNEMANN, KH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03): : 180 - 202
  • [9] Georg G. I., 1993, The Organic Chemistry of (3-Lactams, P295, DOI [10.1002/chin.199425299, DOI 10.1002/CHIN.199425299]
  • [10] Greene T. W., 1999, PROTECTIVE GROUPS OR