MCM-41 heterogenized chiral amines as base catalysts for enantio selective Michael reaction

被引:35
作者
Corma, A
Iborra, S
Rodríguez, I
Iglesias, M
Sánchez, F
机构
[1] Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Valencia 46022, Spain
[2] CSIC, Inst Quim Organ, E-28006 Madrid, Spain
关键词
enantioselective Michael reaction; MCM-41 heterogenized cinchonine; heterogenized cinchonidine; solid chiral base catalyst; enantioselective catalysts;
D O I
10.1023/A:1020531315091
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
Cinchonidine and cinchonine have been grafted onto pure silica MCM-41. It has been shown that both supported alkaloids are active catalysts for the Michael addition of ethyl 2-oxocyclopentanecarboxylate and methyl vinyl ketone, anchored cinchonidine being more active and enantioselective than anchored cinchonine. The study of the influence of the polarity of the solvent and reaction temperature on the optical induction shows that there is not a direct correlation between solvent polarity and enantioselectivity, and the maximum optical yield was obtained between 278 and 273 K.
引用
收藏
页码:237 / 242
页数:6
相关论文
共 48 条
[11]   ASYMMETRIC CATALYSIS .18. ENANTIOSELECTIVE MICHAEL ADDITIONS WITH OPTICALLY-ACTIVE COII/DIAMINE CATALYSTS [J].
BRUNNER, H ;
HAMMER, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (04) :312-313
[12]   CHIRAL INDUCTION IN PHOTOCHEMICAL-REACTIONS .10. THE PRINCIPLE OF ISOINVERSION - A MODEL OF STEREOSELECTION DEVELOPED FROM THE DIASTEREOSELECTIVITY OF THE PATERNO-BUCHI REACTION [J].
BUSCHMANN, H ;
SCHARF, HD ;
HOFFMANN, N ;
PLATH, MW ;
RUNSINK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5367-5373
[13]   THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY [J].
BUSCHMANN, H ;
SCHARF, HD ;
HOFFMANN, N ;
ESSER, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) :477-515
[14]  
CORMA A, 1995, CHIRAL REACTIONS IN HETEROGENEOUS CATALYSIS, P179
[15]   NEW RHODIUM COMPLEXES ANCHORED ON MODIFIED USY ZEOLITES - A REMARKABLE EFFECT OF THE SUPPORT ON THE ENANTIOSELECTIVITY OF CATALYTIC-HYDROGENATION OF PROCHIRAL ALKENES [J].
CORMA, A ;
IGLESIAS, M ;
DELPINO, C ;
SANCHEZ, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1253-1255
[16]   OPTICALLY-ACTIVE COMPLEXES OF TRANSITION-METALS (RH(I), RU(II), CO(II) AND NI(II)) WITH 2-AMINOCARBONYLPYRROLIDINE LIGANDS - SELECTIVE CATALYSTS FOR HYDROGENATION OF PROCHIRAL OLEFINS [J].
CORMA, A ;
IGLESIAS, M ;
DELPINO, C ;
SANCHEZ, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 431 (02) :233-246
[17]   CHIRAL CROWN COMPLEXES CATALYZE MICHAEL ADDITION-REACTIONS TO GIVE ADDUCTS IN HIGH OPTICAL YIELDS [J].
CRAM, DJ ;
SOGAH, GDY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (13) :625-628
[18]   BASIS AND LIMITATIONS OF REACTIVITY-SELECTIVITY PRINCIPLE [J].
GIESE, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (03) :125-136
[19]   A REASSESSMENT OF THE ISOINVERSION PRINCIPLE [J].
HALE, KJ ;
RIDD, JH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) :357-358
[20]   Nonlinear temperature behavior of product ratios in selection processes [J].
Heller, D ;
Buschmann, H ;
Scharf, HD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (16) :1852-1854