HETEROGENEOUS CATALYSIS OF ASYMMETRIC DIELS-ALDER REACTIONS

被引:6
作者
CATIVIELA, C
FRAILE, JM
GARCIA, JI
MAYORAL, JA
PIRES, E
FIGUERAS, F
机构
[1] UNIV ZARAGOZA,CSIC,INST CIENCIA MAT ARAGON,DEPT QUIM ORGAN,E-50009 ZARAGOZA,SPAIN
[2] ENSCM,CHIM ORGAN PHYS & CINET CHIM APL LAB,CNRS,URA 418,F-34053 MONTPELLIER 1,FRANCE
来源
JOURNAL OF MOLECULAR CATALYSIS | 1994年 / 89卷 / 1-2期
关键词
DIELS-ALDER REACTIONS; MENTHOL DERIVATIVES; MONTMORILLONITE CLAYS; ZINC;
D O I
10.1016/0304-5102(93)E0318-B
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Zn(II)-exchanged K10-montmorillonites, activated by several methods, are used as catalysts in the asymmetric Diels-Alder reactions of acrylates of (-)-menthol and (-)-8-phenylmenthol with cyclopentadiene. Calcined clays show a higher catalytic activity and lead to better percentages of diastereomeric excess in the case of acrylate of (-)-menthol. Furthermore, calcined clays are easily recovered with no loss of catalytic properties. In the case of the acrylate of (-)-8-phenylmenthol, the percentages of diastereomeric excess are lower than expected, due to the significant contribution of the non-catalysed reaction.
引用
收藏
页码:159 / 164
页数:6
相关论文
共 25 条
[1]  
ADAMS JM, 1985, INT CLAY C DENVER, P2
[2]   PRODUCT DISTRIBUTION IN DIELS-ALDER ADDITION OF N-BENZYLIDENE ANILINE ANILINE AND ENOL ETHERS [J].
CABRAL, J ;
LASZLO, P .
TETRAHEDRON LETTERS, 1989, 30 (51) :7237-7238
[3]   EFFECT OF CLAY CALCINATION ON CLAY-CATALYZED DIELS-ALDER REACTIONS OF CYCLOPENTADIENE WITH METHYL AND (-)-MENTHYL ACRYLATES [J].
CATIVIELA, C ;
FRAILE, JM ;
GARCIA, JI ;
MAYORAL, JA ;
PIRES, E ;
FIGUERAS, F ;
DEMENORVAL, LC .
TETRAHEDRON, 1992, 48 (31) :6467-6476
[4]   A STUDY ON THE ROLE OF SOLVENT IN CLAY-CATALYZED DIELS-ALDER REACTIONS [J].
CATIVIELA, C ;
FRAILE, JM ;
GARCIA, JI ;
MAYORAL, JA ;
FIGUERAS, F .
JOURNAL OF MOLECULAR CATALYSIS, 1991, 68 (03) :L31-L34
[5]   CLAY-CATALYZED ASYMMETRIC DIELS-ALDER REACTION OF CYCLOPENTADIENE WITH (-)-MENTHYL ACRYLATE [J].
CATIVIELA, C ;
FIGUERAS, F ;
FRAILE, JM ;
GARCIA, JI ;
MAYORAL, JA .
TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :953-956
[6]   FACTORS INFLUENCING THE K10 MONTMORILLONITE-CATALYZED DIELS-ALDER REACTION BETWEEN METHYL ACRYLATE AND CYCLOPENTADIENE [J].
CATIVIELA, C ;
FRAILE, JM ;
GARCIA, JI ;
MAYORAL, JA ;
FIGUERAS, F ;
DEMENORVAL, LC ;
ALONSO, PJ .
JOURNAL OF CATALYSIS, 1992, 137 (02) :394-407
[7]   THERMAL-REACTIONS OF DONOR-ACCEPTOR SYSTEMS .7. HETERO DIELS-ALDER REACTIONS OF ALLENES ON SILICA-GEL SURFACE AND UNDER LIQUID-PHASE CONDITIONS [J].
CONRADS, M ;
MATTAY, J ;
RUNSINK, J .
CHEMISCHE BERICHTE, 1989, 122 (11) :2207-2208
[8]  
Helmchen G, 1986, MODERN SYNTHETIC MET, V4, P261
[9]   THE DIELS-ALDER REACTION OF CYCLOPENTADIENE AND METHYL ACRYLATE ON GAMMA-ALUMINA [J].
HONDROGIANNIS, G ;
PAGNI, RM ;
KABALKA, GW ;
ANOSIKE, P ;
KURT, R .
TETRAHEDRON LETTERS, 1990, 31 (38) :5433-5436
[10]   THE REACTION OF OPTICALLY-ACTIVE MENTHYL ACRYLATE WITH CYCLOPENTADIENE ON GAMMA-ALUMINA [J].
HONDROGIANNIS, G ;
PAGNI, RM ;
KABALKA, GW ;
KURT, R ;
COX, D .
TETRAHEDRON LETTERS, 1991, 32 (21) :2303-2306