A NEW NUCLEOPHILIC ALANINOL SYNTHON FROM SERINE

被引：78
作者：
SIBI, MP
RENHOWE, PA
机构：
[1] Department of Chemistry, North Dakota State University Fargo
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 51期
关键词：
D O I：
10.1016/S0040-4039(00)88501-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new nucleophilic alaninol synthon derived from serine is reported. The utility of this reagent in the stereoselective synthesis of beta,gamma-unsaturated amino alcohols is described.
引用
收藏
页码：7407 / 7410
页数：4
相关论文
共 32 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]  
BAJROWICZ JA, 1985, TETRAHEDRON, V41, P1833
[4]   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
[5]   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
[6]   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
[7]   THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ONEIL, IA ;
SCHOFIELD, C ;
SPIVEY, AC ;
SWEENEY, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854
[8]  
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[9]   ENANTIOSPECIFIC SYNTHESIS OF D-ALPHA,OMEGA-DIAMINOALKANOIC ACIDS [J].
BEAULIEU, PL ;
SCHILLER, PW .
TETRAHEDRON LETTERS, 1988, 29 (17) :2019-2022
[10]   SYNTHESIS OF ALPHA-AMINO-ACIDS WITH BETA,GAMMA-UNSATURATED SIDE-CHAINS [J].
CASTELHANO, AL ;
HORNE, S ;
TAYLOR, GJ ;
BILLEDEAU, R ;
KRANTZ, A .
TETRAHEDRON, 1988, 44 (17) :5451-5466
1234