The first case of asymmetric induction in intramolecular nitrile imine cycloadditions: synthesis of enantiopure 3-substituted 6-oxo-2,3,3a,5-tetrahydro-4-carbomethoxy-furo[3,4-c]pyrazoles

被引:19
作者
Broggini, G
Garanti, L
Molteni, G
Zecchi, G
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] Univ Insubria, Dipartimento Sci Chim Fisiche & Matemat, I-22100 Como, Italy
关键词
D O I
10.1016/S0957-4166(99)00012-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Intramolecular cycloaddition of homochiral nitrile imines 5, generated in situ from base treatment of the corresponding hydrazonoyl chlorides 4, involves diastereoselective formation of the title compounds in the enantiomerically pure form. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码:487 / 492
页数:6
相关论文
共 26 条
  • [1] ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253
  • [2] [Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
  • [3] [Anonymous], 1984, 13 DIPOLAR CYCLOADDI
  • [4] [Anonymous], 1991, Comprehensive Organic Synthesis
  • [5] BALASUBRAMANIAN N, 1985, ORG PREP P INT, V17, P25
  • [6] First highly regio- and diastereoselective synthesis of Δ2-pyrazolines by [3+2] cycloaddition of chiral non-racemic Fischer carbene complexes with nitrilimines
    Barluenga, J
    Fernández-Marí, F
    Aguilar, E
    Viado, AL
    Olano, B
    [J]. TETRAHEDRON LETTERS, 1998, 39 (27) : 4887 - 4890
  • [7] BATTERHAM TJ, 1971, NMR SPECTRA SIMPLE H
  • [8] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF LEVOGLUCOSENONE
    BLAKE, AJ
    COOK, TA
    FORSYTH, AC
    GOULD, RO
    PATON, RM
    [J]. TETRAHEDRON, 1992, 48 (37) : 8053 - 8064
  • [9] Synthesis of bis-(3,5)pyrazolophanes by sequential intermolecular-intramolecular nitrilimine cycloadditions
    Broggini, G
    Garanti, L
    Molteni, G
    Zecchi, G
    [J]. TETRAHEDRON, 1998, 54 (12) : 2843 - 2852
  • [10] MEDIUM-RING AND LARGE-RING HETEROCYCLIC-SYSTEMS BY INTRAMOLECULAR NITRILE IMINE CYCLOADDITIONS
    BROGGINI, G
    BRUCHE, L
    GARANTI, L
    ZECCHI, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (04): : 433 - 438