STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA,BETA-DIAMINO ACIDS, CHIRAL KEY COMPOUNDS IN THE SYNTHESIS OF CONFORMATIONALLY CONSTRAINED PEPTIDOMIMETRICS AND NON-PEPTIDOMIMETICS

被引:28
作者
BADORREY, R [1 ]
CATIVIELA, C [1 ]
DIAZDEVILLEGAS, MD [1 ]
GALVEZ, JA [1 ]
机构
[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN
关键词
D O I
10.1016/0957-4166(95)00368-Y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This work describes an efficient synthesis of enantiomerically pure (R)-2-aminomethylalanine, (R)-2-aminomethylnorvaline, (R)-2-aminomethylvaline, (R)-2-aminomethylleucine and (R)-2-aminomethylphenylalanine by electrophilic amination of chiral 2-cyanoesters with O-(diphenylphosphinyl)hydroxylamine followed by appropiate reduction and hydrolysis.
引用
收藏
页码:2787 / 2796
页数:10
相关论文
共 23 条
[1]   SYNTHESIS OF CYANOCINNAMIC ESTERS BY THE KNOEVENAGEL REACTION [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
SYNTHETIC COMMUNICATIONS, 1990, 20 (20) :3145-3152
[2]  
CATIVIELA C, 1995, TETRAHEDRON-ASYMMETR, V6, P2611
[3]   ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2497-2505
[4]   CHIRAL 2-CYANOCINNAMATES IN CONJUGATE ADDITION ASYMMETRIC ENOLATE TRAPPING REACTIONS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) :1657-1661
[5]   STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - SYNTHESIS OF CHIRAL KEY INTERMEDIATES FOR BETA-LACTAM ANTIBIOTICS [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1465-1468
[6]  
GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991
[7]   IMIDAZOLINES AS AMIDE BOND REPLACEMENTS [J].
GILBERT, IH ;
REES, DC ;
CROCKETT, AK ;
JONES, RCF .
TETRAHEDRON, 1995, 51 (22) :6315-6336
[8]  
HARTWIG W, 1991, SYNTHESIS-STUTTGART, P939
[9]  
IRELAND E, 1973, ORG SYNTH, V5, P171
[10]  
JONES RCF, 1994, TETRAHEDRON-ASYMMETR, V5, P1661