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
[1]   SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].
ARNOLD, LD ;
MAY, RG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241
[2]   CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS [J].
ARNOLD, LD ;
DROVER, JCG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4649-4659
[3]   CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES [J].
ARNOLD, LD ;
KALANTAR, TH ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7105-7109
[4]  
BAJGROWICZ JA, 1984, TETRAHEDRON LETT, V25, P2759, DOI 10.1016/S0040-4039(01)81283-1
[5]   ORGANOCUPRATES IN A NEW SYNTHESIS OF PURE ENANTIOMERIC AMINO-ACIDS [J].
BAJGROWICZ, JA ;
ELHALLAOUI, A ;
JACQUIER, R ;
PIGIERE, C ;
VIALLEFONT, P .
TETRAHEDRON, 1985, 41 (10) :1833-1843
[6]   ASYMMETRIC AMINO-ACID SYNTHESIS - PREPARATION OF THE BETA-ANION DERIVED FROM ASPARTIC-ACID [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :833-834
[7]   NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ROBINSON, NG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155
[8]   AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ ;
SWEENEY, JB .
TETRAHEDRON, 1993, 49 (28) :6309-6330
[9]   CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884
[10]   NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
TETRAHEDRON, 1989, 45 (19) :6309-6318
123456