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 [J].
SOAI, K ;
NIWA, S .
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 [J].
TANNER, D ;
BIRGERSSON, C ;
DHALIWAL, HK .
TETRAHEDRON LETTERS, 1990, 31 (13) :1903-1906
[53]   DESIGN, SYNTHESIS, AND ANTITUMOR ACTIVITY-ABSOLUTE CONFIGURATION RELATIONSHIPS OF PODOPHYLLOTOXIN AZA-ANALOGS [J].
TOMIOKA, K ;
KUBOTA, Y ;
KOGA, K .
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 [J].
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 .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :887-900
[58]  
WILLIAMS RM, 1989, SYNTHESIS OPTICALLY, pCH2