Synthesis of optically active beta,gamma-alkynylglycine derivatives

被引:43
作者
Meffre, P
Gauzy, L
Branquet, E
Durand, P
LeGoffic, F
机构
[1] Lab. de Bioorganique et B., 75231 Paris Cédex 05
关键词
D O I
10.1016/0040-4020(96)00630-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Full results on the first synthesis of optically active beta,gamma-alkynylglycine derivatives from naturally occurring L-serine are described, The methodology uses L-serinal as a key intermediate and allows great versatility in the introduction of N-protective groups and of alkyne substitution. The N-Boc protected beta,gamma-alkynylglycine derivatives described have ee greater than 90%. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:11215 / 11238
页数:24
相关论文
共 102 条
[1]  
Abdulganeeva S.A., 1991, RUSS CHEM REV, V60, P676, DOI [10.1070/RC1991v060n06ABEH001101, DOI 10.1070/RC1991V060N06ABEH001101]
[2]  
ABELES RH, 1983, CHEM ENG NEWS 0919, P48
[3]  
ABELES RH, 1980, PURE APPL CHEM, V53, P149
[4]   STEREOSELECTIVE SYNTHESIS OF BETA,GAMMA-UNSATURATED AMINO-ACIDS [J].
ANGST, C .
PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :373-380
[5]  
[Anonymous], J AM CHEM SOC, V142, P512
[6]   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
[7]   ACID-CATALYZED RACEMIZATION OF 1-(HETEROCYCLYLOXY)-2,3-PROPANEDIOLS [J].
BARLOW, JJ ;
BLOCK, MH ;
HUDSON, JA ;
LEACH, A ;
LONGRIDGE, JL ;
MAIN, BG ;
NICHOLSON, S .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5158-5162
[8]  
BARRETT GC, 1985, CHEM BIOCH AMINO ACI
[9]   FATTY-ACIDS .33. SYNTHESIS OF ALL OCTADECYNOIC ACIDS AND ALL TRANS-OCTADECENOIC ACIDS [J].
BARVE, JA ;
GUNSTONE, FD .
CHEMISTRY AND PHYSICS OF LIPIDS, 1971, 7 (04) :311-+
[10]   SYNTHESIS OF CHIRAL VINYLGLYCINES [J].
BEAULIEU, PL ;
DUCEPPE, JS ;
JOHNSON, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4196-4204