SYNTHESIS OF A NEW-TYPE OF CONFORMATIONALLY CONSTRAINED ALPHA,ALPHA-DISUBSTITUTED-BETA-AMINO ACIDS AND BETA-LACTAMS IN ENANTIOMERICALLY PURE FORM

被引:13
作者
AVENOZA, A
CATIVIELA, C
PARIS, M
PEREGRINA, JM
机构
[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT ORGAN CHEM,E-50009 ZARAGOZA,SPAIN
[2] UNIV LA RIOJA,DEPT CHEM ORGAN CHEM,EDIFICIO CIENT TECN,SECC CIENCIAS,E-26001 LOGRONO,SPAIN
关键词
D O I
10.1016/0957-4166(95)00174-N
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Optically active cis-,8a and 8b, and trans-1-aminomethyl-2-phenylcyclohexane-1-carboxylic acids, 9a and 9b, were obtained starting from 1,3-butadiene using Diels-Alder cycloadditions with chiral (E)-2-cyanocinnamates as key steps and following a protocol of stereocontrolled reactions. Subsequent cyclization of these conformationally constrained p-amino acids led to the corresponding alpha,alpha- disubstituted-beta-lactams 10a, 10b, 11a and 11b in enantiomerically pure forms.
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页码:1409 / 1418
页数:10
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