A NEW ELECTROPHILIC ALANINOL SYNTHON - A GENERAL-ROUTE TO OXAZOLIDINONES OF D-2-AMINO OR (R)-2-AMINO ALCOHOLS FROM L-SERINE

被引:38
作者
SIBI, MP
RUTHERFORD, D
SHARMA, R
机构
[1] Department of Chemistry, North Dakota State University, Fargo
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 13期
关键词
D O I
10.1039/p19940001675
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new electrophilic alaninol synthon, (S)-4-(4'-tolylsulfonyloxymethyl) oxazolidin-2-one, derived from serine, undergoes nucleophilic displacements with Gilman cuprates and/or Grignard/CuX reagents in high yield to provide (R)-4-substituted oxazolidinones.
引用
收藏
页码:1675 / 1678
页数:4
相关论文
共 58 条
  • [51] ENANTIOSELECTIVE ADDITION OF ORGANOZINC REAGENTS TO ALDEHYDES
    SOAI, K
    NIWA, S
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 833 - 856
  • [52] NUCLEOPHILIC RING-OPENING OF C-2-SYMMETRIC AZIRIDINES - SYNTHETIC EQUIVALENTS FOR THE BETA-CATION OF ASPARTIC-ACID
    TANNER, D
    BIRGERSSON, C
    DHALIWAL, HK
    [J]. TETRAHEDRON LETTERS, 1990, 31 (13) : 1903 - 1906
  • [53] DESIGN, SYNTHESIS, AND ANTITUMOR ACTIVITY-ABSOLUTE CONFIGURATION RELATIONSHIPS OF PODOPHYLLOTOXIN AZA-ANALOGS
    TOMIOKA, K
    KUBOTA, Y
    KOGA, K
    [J]. TETRAHEDRON, 1993, 49 (09) : 1891 - 1900
  • [54] TOMIOKA K, 1990, SYNTHESIS-STUTTGART, P541
  • [55] UTSUNOMIYA I, 1992, HETEROCYCLES, V33, P349
  • [56] Whitesides G. M., 1970, J AM CHEM SOC, V92, P1426
  • [57] RENIN INHIBITORS CONTAINING CONFORMATIONALLY RESTRICTED P1-P1' DIPEPTIDE MIMETICS
    WILLIAMS, PD
    PERLOW, DS
    PAYNE, LS
    HOLLOWAY, MK
    SIEGL, PKS
    SCHORN, TW
    LYNCH, RJ
    DOYLE, JJ
    STROUSE, JF
    VLASUK, GP
    HOOGSTEEN, K
    SPRINGER, JP
    BUSH, BL
    HALGREN, TA
    RICHARDS, AD
    KAY, J
    VEBER, DF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) : 887 - 900
  • [58] WILLIAMS RM, 1989, SYNTHESIS OPTICALLY, pCH2