The first example of a (1R,2S,5R)-(-)-menthyl chiral auxiliary in intramolecular nitrilimine cycloadditions:: synthesis of enantiopure pyrazolo[1,5-a][4,1]benzoxazepines and pyrazolo[1,5-a][4,1]benzodiazepines

被引：9
作者：
Molteni, G
Pilati, T
机构：
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] CNR, Ctr Studio Relaz Tra Struttura & Reatt Chim, I-20133 Milan, Italy
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 20期
关键词：
D O I：
10.1016/S0957-4166(99)00422-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
By using (1R, 2S, 5R)-(-)-menthyl as a chiral auxiliary, we have developed a synthesis of hydrazonoyl chlorides 2 and 8, treatment of which with silver carbonate promoted the in situ generation of the corresponding nitrilimines 3 and 9. The latter underwent intramolecular cycloaddition giving, respectively, enantiopure pyrazolo[1,5a] [4,1]benzoxazepines 4,5 and pyrazolo[1,5-a][4,1]benzodiazepines 10. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码：3873 / 3876
页数：4
相关论文
共 12 条
  • [1] SIR92 - a program for automatic solution of crystal structures by direct methods
    ALTOMARE, A
    CASCARANO, G
    GIACOVAZZO, G
    GUAGLIARDI, A
    BURLA, MC
    POLIDORI, G
    CAMALLI, M
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 : 435 - 435
  • [2] 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
  • [3] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF LEVOGLUCOSENONE
    BLAKE, AJ
    COOK, TA
    FORSYTH, AC
    GOULD, RO
    PATON, RM
    [J]. TETRAHEDRON, 1992, 48 (37) : 8053 - 8064
  • [4] Stereoselective intramolecular cycloadditions of homochiral nitrile imines:: synthesis of enantiomerically pure 3,3a-dihydro-pyrazolo[1,5-a][1,4] benzodiazepine-6(4H)-ones
    Broggini, G
    Garanti, L
    Molteni, G
    Pilati, T
    Ponti, A
    Zecchi, G
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (11) : 2203 - 2212
  • [5] 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
    Broggini, G
    Garanti, L
    Molteni, G
    Zecchi, G
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (03) : 487 - 492
  • [6] 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
  • [7] BROGGINI G, 1994, HETEROCYCLES, V38, P291
  • [8] Nitrilimines: Evidence for the allenic structure in solution, experimental and ab initio studies of the barrier to racemization, and first diastereoselective [3+2]-cycloaddition
    Faure, JL
    Reau, R
    Wong, MW
    Koch, R
    Wentrup, C
    Bertrand, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) : 2819 - 2824
  • [9] Diastereoselective 1,3-dipolar cycloaddition of nitrilimines to gamma-oxygenated alpha,beta-unsaturated enones and esters
    Grubert, L
    Galley, G
    Patzel, M
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (04) : 1137 - 1148
  • [10] Kunz H, 1999, CHIRAL AUXILIARIES C
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