ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS USING A BETA-ALANINE DERIVATIVE WITH 2 CHIRAL HANDLES

被引:7
作者
AKSSIRA, M
BOUMZEBRA, M
KASMI, H
ROUMESTANT, ML
VIALLEFONT, P
机构
[1] UNIV MONTPELLIER 2,CNRS,URA 468,F-34095 MONTPELLIER 5,FRANCE
[2] UNIV ABDELMALEK ESSAADI,FAC SCI,CHIM ORGAN LAB,TETOUAN,MOROCCO
关键词
AMINO ACIDS; BETA-AMINO ACID; ASYMMETRIC SYNTHESIS; SCHIFF BASE; 2-HYDROXYPINAN-3-ONE; MENTHOL;
D O I
10.1007/BF00808448
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Enantiomerically pure alpha-substituted beta-amino acids have been synthesized, the key step being the diastereoselective alkylation of a beta-alanine derivative with two chiral handles (1S,2R,5S)-menthyl N-[(1S,2S,5S)-2-hydroxypinan-3-ylidene] beta-alaninate.
引用
收藏
页码:79 / 81
页数:3
相关论文
共 10 条
[1]   ABSOLUTE CONFIGURATION OF ALPHA-METHYL-BETA-ALANINE [J].
BALENOVIC, K ;
BREGANT, N .
TETRAHEDRON, 1959, 5 (01) :44-47
[2]  
BOUMZEBRA M, 1988, TETRAHEDRON, V44, P5319
[3]  
DREY CNC, 1985, CHEM BIOCH AMINO ACI, P25
[4]  
ELMARINI A, 1992, SYNTHESIS-STUTTGART, P1104
[5]   ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS .2. PREPARATION OF THE LIKE STEREOISOMERS OF 2-METHYL-3-AMINOBUTANOIC ACID AND 2-BENZYL-3-AMINOBUTANOIC ACID [J].
JUARISTI, E ;
ESCALANTE, J ;
LAMATSCH, B ;
SEEBACH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2396-2398
[6]  
JUARISTI E, 1992, TETRAHEDRON-ASYMMETR, V3, P323
[7]   SELF-REPRODUCTION OF CHIRALITY - ASYMMETRIC-SYNTHESIS OF BETA-ARYL-BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES [J].
KONOPELSKI, JP ;
CHU, KS ;
NEGRETE, GR .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1355-1357
[8]   DOUBLE ASYMMETRIC-SYNTHESIS AND A NEW STRATEGY FOR STEREOCHEMICAL CONTROL IN ORGANIC-SYNTHESIS [J].
MASAMUNE, S ;
CHOY, W ;
PETERSEN, JS ;
SITA, LR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1985, 24 (01) :1-30
[9]   ALKYLATION AND PROTONATION OF CHIRAL SCHIFF-BASES - DIASTEREOSELECTIVITY AS A FUNCTION OF THE NATURE OF REACTANTS [J].
TABCHEH, M ;
ELACHQAR, A ;
PAPPALARDO, L ;
ROUMESTANT, ML ;
VIALLEFONT, P .
TETRAHEDRON, 1991, 47 (26) :4611-4618
[10]  
Williams R.M., 1989, ORGANIC CHEM SERIES, V1