ASYMMETRIC-SYNTHESIS OF EXO-NORBORNANE-2-CARBOXYLIC ACIDS

被引:7
作者
AVENOZA, A [1 ]
BUENO, MP [1 ]
CATIVIELA, C [1 ]
MAYORAL, JA [1 ]
机构
[1] COLEGIO UNIV LA RIOJA,DEPT QUIM ORGAN,E-26001 LOGRONO,SPAIN
关键词
D O I
10.1016/S0957-4166(00)80270-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction between N-acryloyl-N-methyl-L-alanine methyl ester and cyclopentadiene is studied. The configuration of the cycloadducts preferably obtained depends on the reaction conditions and the Lewis acid used as a catalyst. In TiCl4-catalyzed reactions, high exo:endo ratios and good diastereomeric excesses in exo cycloadducts are obtained under several conditions. So an interesting method for the asymmetric synthesis of derivatives of exo-norbornane-2-carboxylic acid is described.
引用
收藏
页码:343 / 346
页数:4
相关论文
共 8 条
[1]  
BERNSON JA, 1961, J AM CHEM SOC, V83, P3986
[2]   NATURAL AMINO-ACIDS AS CHIRAL AUXILIARIES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].
BUENO, MP ;
CATIVIELA, C ;
MAYORAL, JA ;
AVENOZA, A ;
CHARRO, P ;
ROY, MA ;
ANDRES, JM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (11) :2826-2829
[3]   ASYMMETRIC DIELS-ALDER REACTION OF ACRYLAMIDES HAVING TRANS-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES [J].
KAWANAMI, Y ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (11) :4190-4192
[4]  
KRIMSE W, 1983, J AM CHEM SOC, V105, P950
[5]   EFFECT OF ASYMMETRIC CENTERS ON FREE RADICAL POLYMERIZATION AND PROPERTIES OF POLYMERS - METHACRYLYL ALANINE, METHACRYLYL GLUTAMIC ACID, ACRYLYL GLUTAMIC ACID, AND THEIR POLYMERS [J].
KULKARNI, RK ;
MORAWETZ, H .
JOURNAL OF POLYMER SCIENCE, 1961, 54 (160) :491-&
[6]   STEREOCHEMICAL VARIATIONS IN THE DIELS-ALDER REACTIONS OF SILOXYDIENES WITH N,N-DIMETHYL ACRYLAMIDE - A REMARKABLE INFLUENCE OF THE LEWIS ACID CATALYST [J].
LAMYSCHELKENS, H ;
GIOMI, D ;
GHOSEZ, L .
TETRAHEDRON LETTERS, 1989, 30 (43) :5887-5890
[7]   CONCERNING THE MECHANISM OF THE ASYMMETRIC DIELS-ALDER REACTION - 1ST CRYSTAL-STRUCTURE ANALYSIS OF A LEWIS ACID COMPLEX OF A CHIRAL DIENOPHILE [J].
POLL, T ;
METTER, JO ;
HELMCHEN, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :112-114