Rapid entry to enantiopure carbacepham derivatives via Lewis acid promoted carbonyl-ene cyclization of 2-azetidinone-tethered alkenylaldehydes

被引:15
作者
Alcaide, B [1 ]
Pardo, C [1 ]
Rodríguez-Ranera, C [1 ]
Rodríguez-Vicente, A [1 ]
机构
[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
D O I
10.1021/ol016871a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Lewis acid promoted types I and II carbonyl-ene cyclizations of 2-azetidinone-tethered alkenylaldehydes are used for the rapid, highly diastereoselective synthesis of polyfunctionalized, enantiomerically pure carbacepham derivatives.
引用
收藏
页码:4205 / 4208
页数:4
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共 30 条
  • [21] Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the beta-lactam synthon method
    Ojima, I
    Delaloge, F
    [J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) : 377 - 386
  • [22] ASYMMETRIC ALKYLATIONS OF A PHENYLALANYLGLYCINATE EQUIVALENT - NOVEL ROUTE TO DIPEPTIDES BEARING ALPHA-ALKYL-ALPHA-AMINO ACID RESIDUES
    OJIMA, I
    KOMATA, T
    QIU, XG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 770 - 774
  • [23] INTRA-MOLECULAR ENE REACTIONS IN ORGANIC-SYNTHESIS
    OPPOLZER, W
    SNIECKUS, V
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07): : 476 - 486
  • [24] Page M.I., 1992, CHEM BETA LACTAMS
  • [25] Practical access to carbacephem intermediates via asymmetric [2+2] ketene-imine cycloaddition
    Palomo, C
    Ganboa, I
    Kot, A
    Dembkowski, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) : 6398 - 6400
  • [26] From β-lactams to α- and β-amino acid derived peptides
    Palomo, C
    Aizpurua, JM
    Ganboa, I
    Oiarbide, M
    [J]. AMINO ACIDS, 1999, 16 (3-4) : 321 - 343
  • [27] Snider B. B., COMPREHENSIVE ORGANI, V2, P527, DOI DOI 10.1016/B978-0-08-052349-1.00040-8
  • [28] Southgate R., 1994, Contemp. Org. Synth., V1, p417 431, DOI [DOI 10.1039/CO9940100417, 10.1039/CO9940100417]
  • [29] Southgate R., 1993, RECENT PROGR CHEM SY, V2, P621, DOI DOI 10.1002/ADSC.201400191
  • [30] STUDIES ON LACTAMS .81. ENANTIOSPECIFIC SYNTHESIS AND ABSOLUTE-CONFIGURATION OF SUBSTITUTED BETA-LACTAMS FROM D-GLYCERALDEHYDE ACETONIDE
    WAGLE, DR
    GARAI, C
    CHIANG, J
    MONTELEONE, MG
    KURYS, BE
    STROHMEYER, TW
    HEGDE, VR
    MANHAS, MS
    BOSE, AK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) : 4227 - 4236