Heterogenization of a chiral bis(oxazoline) catalyst by grafting onto silica

被引:81
作者
Rechavi, D [1 ]
Lemaire, M [1 ]
机构
[1] UCBL, CPE, Lab Catalyse & Synth Organ, F-69622 Villeurbanne, France
关键词
D O I
10.1021/ol016117p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We report here the first heterogenization of a bis(oxazolins) ligand on an inorganic (silica) surface. The activity and enantioselectivity of this new material as a catalyst for the Diels-Alder reaction were checked, and it was shown that under certain conditions enantioselectivities similar to those of the homogeneous catalyst are reached. It was also shown that under these conditions the catalyst can be recycled without loss of activity or selectivity.
引用
收藏
页码:2493 / 2496
页数:4
相关论文
共 28 条
[1]   Spectroscopic study of the structure of bis(oxazoline)copper complexes in solution and immobilized on laponite clay.: Influence of the structure on the catalytic performance [J].
Alonso, PJ ;
Fraile, JM ;
García, J ;
García, JI ;
Martínez, JI ;
Mayoral, JA ;
Sánchez, MC .
LANGMUIR, 2000, 16 (13) :5607-5612
[2]   Poly(ethylene glycol)-supported bisoxazolines as ligands for catalytic enantioselective synthesis [J].
Annunziata, R ;
Benaglia, M ;
Cinquini, M ;
Cozzi, F ;
Pitillo, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3160-3166
[3]  
Bae SJ, 2000, CHEM COMMUN, P31
[4]   Polymer-supported bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions [J].
Burguete, MI ;
Fraile, JM ;
García, JI ;
García-Verdugo, E ;
Luis, SV ;
Mayoral, JA .
ORGANIC LETTERS, 2000, 2 (24) :3905-3908
[5]   DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].
COREY, EJ ;
IMAI, N ;
ZHANG, HY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729
[6]   HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX [J].
COREY, EJ ;
ISHIHARA, K .
TETRAHEDRON LETTERS, 1992, 33 (45) :6807-6810
[7]   Application of indane-derived C-2-symmetric bis(oxazolines) in two-point binding asymmetric Diels-Alder reactions [J].
Davies, IW ;
Senanayake, CH ;
Larsen, RD ;
Verhoeven, TR ;
Reider, PJ .
TETRAHEDRON LETTERS, 1996, 37 (11) :1725-1726
[8]  
DAVIES IW, 1996, J CHEM SOC CHEM COMM, P1753
[9]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[10]   Chiral bis(oxazoline)copper(II) complexes as Lewis acid catalysts for the enantioselective Diels-Alder reaction [J].
Evans, DA ;
Miller, SJ ;
Lectka, T ;
von Matt, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7559-7573