Stereoselective synthesis of homochiral pyrrolidinones and cis,cis-bis-beta-lactams from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol.

被引：37
作者：
Jayaraman, M
Puranik, VG
Bhawal, BM
机构：
[1] NATL CHEM LAB,DIV ORGAN CHEM SYNTH,PUNE 411008,MAHARASHTRA,INDIA
[2] NATL CHEM LAB,DIV PHYS CHEM,PUNE 411008,MAHARASHTRA,INDIA
来源：
TETRAHEDRON | 1996年 / 52卷 / 27期
关键词：
D O I：
10.1016/0040-4020(96)00462-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The homochiral beta-lactams described in the preceding paper undergone an acid catalyzed rearrangement to 4-aminopyrrolidinones 2a-e in excellent yields. A diastereoselective synthesis of cis,cis-bis-beta-lactams 13 & 14 has been achieved by using imines bearing a beta-lactam back bone in good yields and good to excellent selectivities. Copyright (C) 1996 Elsevier Science Ltd
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页码：9005 / 9016
页数：12
相关论文
共 27 条
  • [1] ASZODI J, 1989, RECENT ADV CHEM BETA, P350
  • [2] BALDWIN JE, 1995, TETRAHEDRON, V51, P11581
  • [3] ASYMMETRIC-SYNTHESIS OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED 2-AZETIDINONES - STRATEGY BASED ON USE OF D-GLUCOSAMINE AS A CHIRAL AUXILIARY IN THE STAUDINGER REACTION
    BARTON, DHR
    GATEAUOLESKER, A
    ANAYAMATEOS, J
    CLEOPHAX, J
    GERO, SD
    CHIARONI, A
    RICHE, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3211 - 3212
  • [4] STUDIES ON LACTAMS .75. ABSOLUTE-CONFIGURATION OF ALPHA-SUBSTITUTED BETA-LACTAMS FROM D-GLYCERALDEHYDE ACETONIDE
    BOSE, AK
    HEGDE, VR
    WAGLE, DR
    BARI, SS
    MANHAS, MS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (02) : 161 - 163
  • [5] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
    COREY, EJ
    VENKATESWARLU, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +
  • [6] 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
  • [7] SYNTHESIS OF A NEW PROTECTED LACTAM-BRIDGED DIPEPTIDE
    EDE, NJ
    RAE, ID
    HEARN, MTW
    [J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6071 - 6074
  • [8] FACILE SYNTHESES AND REARRANGEMENTS OF PEPTIDE DERIVED BETA-LACTAMS
    FAROUZ, F
    MILLER, MJ
    [J]. TETRAHEDRON LETTERS, 1991, 32 (28) : 3305 - 3308
  • [9] NRCVAX - AN INTERACTIVE PROGRAM SYSTEM FOR STRUCTURE-ANALYSIS
    GABE, EJ
    LEPAGE, Y
    CHARLAND, JP
    LEE, FL
    WHITE, PS
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 : 384 - 387
  • [10] Georg G. I., 1993, The Organic Chemistry of (3-Lactams, P295, DOI [10.1002/chin.199425299, DOI 10.1002/CHIN.199425299]
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