A practical synthesis of (R)-3-chlorostyrene oxide starting from 3-chloroethylbenzene

被引:24
作者
Tanaka, K [1 ]
Yasuda, M [1 ]
机构
[1] Mitsubishi Chem Corp, Yokohama Res Ctr, Aoba Ku, Kanagawa 2278502, Japan
关键词
D O I
10.1016/S0957-4166(98)00337-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel and practical synthesis of (R)-3-chlorostyrene oxide (-)-1 was achieved starting from commercially available 3-chloroethylbenzene 3. Enantiopure (-)-3-chlorostyrene bromohydrin (-)-5 was obtained by the treatment of racemic (+/-)-5 with lipase QL in the presence of acylating reagents. 3-Chloro-alpha,beta-dibromoethylbenzene 4, a precursor of (+/-)-5, was synthesized via the expeditious bromination of 3 which was developed by these authors. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3275 / 3282
页数:8
相关论文
共 15 条
  • [1] SYNTHESIS OF THE POTENT AND SELECTIVE ATYPICAL BETA-ADRENERGIC AGONIST SR 59062A
    BADONE, D
    GUZZI, U
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (16) : 1921 - 1924
  • [2] ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS
    BIANCHI, D
    CESTI, P
    BATTISTEL, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5531 - 5534
  • [3] DISODIUM (R,R)-5-[2-[[2-(3-CHLOROPHENYL)-2-HYDROXYETHYL]AMINO]PROPYL]-1,3-BENZODIOXOLE-2,2-DICARBOXYLATE (CL 316,243) - A POTENT BETA-ADRENERGIC AGONIST VIRTUALLY SPECIFIC FOR BETA-3 RECEPTORS - A PROMISING ANTIDIABETIC AND ANTIOBESITY AGENT
    BLOOM, JD
    DUTIA, MD
    JOHNSON, BD
    WISSNER, A
    BURNS, MG
    LARGIS, EE
    DOLAN, JA
    CLAUS, TH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (16) : 3081 - 3084
  • [4] BRITTEN AZ, 1968, CHEM IND-LONDON, P771
  • [5] SYNTHESIS AND BETA-ADRENERGIC ACTIVITY OF ATYPICAL BETA-ADRENERGIC PHENYLETHANOLAMINOTETRALIN STEREOISOMERS
    CECCHI, R
    CROCI, T
    BOIGEGRAIN, R
    BOVERI, S
    BARONI, M
    BOCCARDI, G
    GUIMBARD, JP
    GUZZI, U
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1994, 29 (04) : 259 - 267
  • [6] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [7] FABIO RD, 1995, BIOORG MED CHEM LETT, V5, P551
  • [8] ASYMMETRIC-SYNTHESIS OF FR165914 - A NOVEL BETA(3)-ADRENERGIC AGONIST WITH A BENZOCYCLOHEPTENE STRUCTURE
    HATTORI, K
    NAGANO, M
    KATO, T
    NAKANISHI, I
    IMAI, K
    KINOSHITA, T
    SAKANE, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (23) : 2821 - 2824
  • [9] MATSUYAMA A, 1994, Patent No. 0611826
  • [10] MULTIGRAM LIPASE-CATALYZED ENANTIOSELECTIVE ACYLATION IN THE SYNTHESIS OF THE 4 STEREOISOMERS OF A NEW BIOLOGICALLY-ACTIVE ALPHA-ARYL-4-PIPERIDINEMETHANOL DERIVATIVE
    NIEDUZAK, TR
    MARGOLIN, AL
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (02) : 113 - 122