CLAY-CATALYZED ASYMMETRIC DIELS-ALDER REACTION OF CYCLOPENTADIENE WITH (-)-MENTHYL ACRYLATE

被引:24
作者
CATIVIELA, C [1 ]
FIGUERAS, F [1 ]
FRAILE, JM [1 ]
GARCIA, JI [1 ]
MAYORAL, JA [1 ]
机构
[1] ECOLE NATL SUPER CHIM MONTPELLIER,CNRS,URA 418,CHIM ORGAN PHYS & CINET LAB,F-34053 MONTPELLIER 1,FRANCE
关键词
D O I
10.1016/S0957-4166(00)86134-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Zn(II)-exchanged K10 montmorillonite is shown to be an efficient catalyst for the reaction between cyclopentadiene and (-)-menthyl acrylate, leading to the 1R,2R-cycloadduct with good chemical yield, high % d.e. and excellent endo/exo selectivity.
引用
收藏
页码:953 / 956
页数:4
相关论文
共 24 条
[1]  
BOECKMAN RV, 1980, J ORG CHEM, V45, P754
[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]  
CATIVIELA C, IN PRESS J MOL CATAL
[4]   SYNTHESIS OF DIASTEREOMERIC MIXTURE (2RS)-2-[(1R)-3-CYCLOHEXENYL] PROPANAL [J].
CEDER, O ;
NILSSON, HG .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (09) :908-910
[5]   CLAY CATALYSIS OF THE NONAQUEOUS DIELS-ALDER REACTION AND THE IMPORTANCE OF HUMIDITY CONTROL [J].
COLLET, C ;
LASZLO, P .
TETRAHEDRON LETTERS, 1991, 32 (25) :2905-2908
[6]   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
[7]   PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].
COREY, EJ ;
ENSLEY, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909
[8]   STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL) [J].
COREY, EJ ;
WEINSHENKER, NM ;
SCHAAF, TK ;
HUBER, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (20) :5675-+
[9]  
FARMER RF, 1968, J ORG CHEM, V31, P2418
[10]  
Helmchen G, 1986, MODERN SYNTHETIC MET, V4, P261