Convenient and stereospecific homologation of N-fluorenyl-methoxycarbonyl-alpha-amino acids to their beta-homologues

被引:47
作者
Leggio, A [1 ]
Liguori, A [1 ]
Procopio, A [1 ]
Sindona, G [1 ]
机构
[1] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87030 ARCAVACATA,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 13期
关键词
D O I
10.1039/a700731k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very simple approach to the enantioselective homologation of alpha-amino acids is presented which is based on the formation of N-Fmoc-aminoacyldiazomethanes with nearly quantitative yields and on the complete retention of both chiral configuration and N-terminal protecting group in the overall transformation.
引用
收藏
页码:1969 / 1971
页数:3
相关论文
共 17 条
[1]  
[Anonymous], COMPREHENSIVE ORGANI
[2]  
Arndt F., 1943, ORG SYNTH, V2, P165
[3]   Kainic acid as conformationally constrained glutamic acid analog in peptide synthesis [J].
Artuso, F ;
Sindona, G ;
Athanassopoulos, C ;
Stavropoulos, G ;
Papaioannou, D .
TETRAHEDRON LETTERS, 1995, 36 (51) :9309-9312
[4]  
Backer H. J., 1963, ORG SYNTH, VIV, P250
[5]   HERSTELLUNG VON ALPHA-AMINOSAUREESTERN DURCH ALKOHOLYSE DER METHYLESTER [J].
BRENNER, M ;
HUBER, W .
HELVETICA CHIMICA ACTA, 1953, 36 (05) :1109-1115
[6]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].
CARPINO, LA ;
COHEN, BJ ;
STEPHENS, KE ;
SADATAALAEE, SY ;
TIEN, JH ;
LANGRIDGE, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734
[7]  
FINSOO A, 1995, TETRAHEDRON ASYNUMET, V6, P2245
[8]   SHORT, ENANTIOGENIC SYNTHESES OF (-)-INDOLIZIDINE 167B AND (+)-MONOMORINE [J].
JEFFORD, CW ;
TANG, Q ;
ZASLONA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3513-3518
[9]   Synthesis of 4'-aza analogues of 2',3'-dideoxythymidine by 1,3-dipolar cycloadditions of nitrones to 1-N-vinyl-thymine [J].
Leggio, A ;
Liguori, A ;
Procopio, A ;
Siciliano, C ;
Sindona, G .
TETRAHEDRON LETTERS, 1996, 37 (08) :1277-1280
[10]  
NEEMAN M, 1973, ORG SYNTH, V5, P245