Application of the evans aziridination procedure to 2-substituted acrylates and cinnamates:: An expedient route to α-substituted α- and β-amino acids

被引:52
作者
Dauban, P [1 ]
Dodd, RH [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4039(98)01132-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of the title compounds with Phl=NSO2Ar (Ar = p-tolyl or p-nitrophenyl) in the presence of catalytic copper (II) triflate in acetonitrile gave the corresponding 2 and/or 3-substituted aziridine-2-carboxylates in generally; good yields. The latter, on reaction with nucleophiles, gave alpha-substituted alpha- or beta-amino acids depending on the pattern of substitution on the aziridine ring. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5739 / 5742
页数:4
相关论文
共 30 条
  • [1] Enantiospecific alkylations of alanine
    Alonso, F
    Davies, SG
    Elend, AS
    Haggitt, JL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02): : 257 - 264
  • [2] THE DEVELOPMENT OF A NOVEL SERIES OF NONPEPTIDE TACHYKININ NK3 RECEPTOR-SELECTIVE ANTAGONISTS
    BODEN, P
    EDEN, JM
    HODGSON, J
    HORWELL, DC
    PRITCHARD, MC
    RAPHY, J
    SUMANCHAUHAN, N
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) : 1773 - 1778
  • [3] Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - The asymmetric synthesis of alpha,alpha-disubstituted amino acids
    Burgaud, BGM
    Horwell, DC
    Padova, A
    Pritchard, MC
    [J]. TETRAHEDRON, 1996, 52 (40) : 13035 - 13050
  • [4] DESIGN AND SYNTHESIS OF A CONFORMATIONALLY RESTRICTED CYSTEINE PROTEASE INHIBITOR
    CHENG, HM
    KEITZ, P
    JONES, JB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7671 - 7676
  • [5] 2-methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of alpha-methylphenylalanine and alpha-methyl-beta-phenylserine
    Davis, FA
    Liu, H
    Reddy, GV
    [J]. TETRAHEDRON LETTERS, 1996, 37 (31) : 5473 - 5476
  • [6] ASYMMETRIC-SYNTHESIS OF THE SQUALENE SYNTHASE INHIBITOR ZARAGOZIC ACID-C
    EVANS, DA
    BARROW, JC
    LEIGHTON, JL
    ROBICHAUD, AJ
    SEFKOW, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12111 - 12112
  • [7] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
    EVANS, DA
    FAUL, MM
    BILODEAU, MT
    ANDERSON, BA
    BARNES, DM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
  • [8] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES
    FUKUYAMA, T
    JOW, CK
    CHEUNG, M
    [J]. TETRAHEDRON LETTERS, 1995, 36 (36) : 6373 - 6374
  • [9] Goodman M., 1995, Burger ' s Medicinal Chemistry and Drug Discovery, VI, P803
  • [10] Grandel R, 1998, EUR J ORG CHEM, V1998, P409, DOI 10.1002/(SICI)1099-0690(199802)1998:2<409::AID-EJOC409>3.0.CO