AN EFFICIENT AND PRACTICAL SYNTHESIS OF L-ALPHA-AMINO ACIDS USING (R)-PHENYLGLYCINOL AS A CHIRAL AUXILIARY

被引:51
作者
INABA, T
KOZONO, I
FUJITA, M
OGURA, K
机构
[1] CHIBA UNIV, FAC ENGN, DEPT APPL CHEM, 1-33 YAYOICHO, INAGE KU, CHIBA 263, JAPAN
[2] CHIBA UNIV, GRAD SCH SCI & TECHNOL, INAGE KU, CHIBA 263, JAPAN
关键词
D O I
10.1246/bcsj.65.2359
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
L-alpha-Amino acids including L-alpha-arylglycines were conveniently and stereoselectively synthesized via the alpha-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide. The stereoselectivity of these alpha-amino carbonitriles was thermodynamically controlled.
引用
收藏
页码:2359 / 2365
页数:7
相关论文
共 25 条
[1]   STEREOSPECIFIC SYNTHESIS OF 2-AMINO-3-FLUORONITRILES - PREPARATION OF BETA-FLUORO-ALPHA-AMINO ACIDS AND ESTERS [J].
AYI, AI ;
GUEDJ, R .
JOURNAL OF FLUORINE CHEMISTRY, 1984, 24 (02) :137-151
[2]   HERSTELLUNG VON ALPHA-AMINOSAUREESTERN DURCH ALKOHOLYSE DER METHYLESTER [J].
BRENNER, M ;
HUBER, W .
HELVETICA CHIMICA ACTA, 1953, 36 (05) :1109-1115
[3]  
CHAKRABORTY TK, 1991, TETRAHEDRON LETT, V32, P7579
[4]   SYNTHESIS OF (S)-(+)-2-AMINO-3-(1-ADAMANTYL)-PROPIONIC ACID (L-(+)-ADAMANTYLALANINE,ADA) AS A FAT OR SUPER ANALOG OF LEUCINE AND PHENYLALANINE [J].
DO, KQ ;
THANEI, P ;
CAVIEZEL, M ;
SCHWYZER, R .
HELVETICA CHIMICA ACTA, 1979, 62 (04) :956-964
[5]   REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].
ELAMIN, B ;
ANANTHARAMAIAH, GM ;
ROYER, GP ;
MEANS, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444
[6]  
FAUCHERE JL, 1981, INT J PEPT PROT RES, V18, P249
[7]   SYNTHESIS, ENZYMIC DEGRADATION, LIPOPHILIC PROPERTIES, AND BIOLOGICAL-ACTIVITY OF [D-ALANINE2, TERT-BUTYLGLYCINE5]ENKEPHALIN AMIDE [J].
FAUCHERE, JL ;
PETERMANN, C .
HELVETICA CHIMICA ACTA, 1980, 63 (04) :824-831
[8]   ACYCLIC STEREOSELECTION IN THE ALKYLATION OF CHIRAL DIPOLE-STABILIZED ORGANOLITHIUMS - A SELF-IMMOLATIVE CHIRALITY TRANSFER PROCESS FOR THE SYNTHESIS OF PRIMARY AMINES [J].
GAWLEY, RE ;
REIN, K ;
CHEMBURKAR, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3002-3004
[9]   STERICALLY CONTROLLED SYNTHESES OF OPTICALLY-ACTIVE ORGANIC COMPOUNDS .19. ASYMMETRIC SYNTHESES OF AMINO-ACIDS BY STRECKER REACTION [J].
HARADA, K ;
OKAWARA, T ;
MATSUMOT.K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (06) :1865-1868
[10]   ASYMMETRIC SYNTHESIS OF ALPHA-AMINO-ACIDS BY STRECKER SYNTHESIS [J].
HARADA, K .
NATURE, 1963, 200 (491) :1201-&