Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen)manganese complexes

被引:178
作者
Minutolo, F
Pini, D
Petri, A
Salvadori, P
机构
[1] C.N.R. Ctr. Studi Macromolecole S., Dipto. di Chim. e Chim. Industriale, Università di Pisa, I-56126 Pisa
[2] Scuola Normale Superiore, I-56127 Pisa
关键词
D O I
10.1016/0957-4166(96)00284-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of three different polymer-bound chiral Mn-salen complexes (Poly-1, -2a, -2b) is reported, along with their application as recyclable catalysts in heterogeneous asymmetric epoxidation with mCPBA/NMO of several unfunctionalized olefins. The introduction of a spacing group between the polymeric chain and the metal centre (Poly-2a and -2b) considerably increased the enantioselectivity of the process. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2293 / 2302
页数:10
相关论文
共 24 条
[1]   ENANTIOSELECTIVE EPOXIDATION OF 2,2-DIMETHYL-2H-CHROMENES BY DIMETHYLDIOXIRANE AND JACOBSENS MN(III)SALEN CATALYSTS [J].
ADAM, W ;
JEKO, J ;
LEVAI, A ;
NEMES, C ;
PATONAY, T ;
SEBOK, P .
TETRAHEDRON LETTERS, 1995, 36 (21) :3669-3672
[2]  
DE BB, 1995, TETRAHEDRON-ASYMMETR, V6, P2105
[3]   ASYMMETRIC INDUCTION IN THE BASE-CATALYZED REACTIONS USING POLYMER-SUPPORTED QUININES WITH SPACER GROUPS [J].
INAGAKI, M ;
HIRATAKE, J ;
YAMAMOTO, Y ;
ODA, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (11) :4121-4126
[4]   PROTECTION AND POLYMERIZATION OF FUNCTIONAL MONOMERS .13. ANIONIC LIVING POLYMERIZATION OF TERT-BUTYL 4-VINYLBENZOATE [J].
ISHIZONE, T ;
HIRAO, A ;
NAKAHAMA, S .
MACROMOLECULES, 1989, 22 (07) :2895-2901
[5]  
Jacobsen E. N., 1993, CATALYTIC ASYMMETRIC
[6]   HIGHLY ENANTIOSELECTIVE EPOXIDATION CATALYSTS DERIVED FROM 1,2-DIAMINOCYCLOHEXANE [J].
JACOBSEN, EN ;
ZHANG, W ;
MUCI, AR ;
ECKER, JR ;
DENG, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7063-7064
[7]  
JACOBSEN EN, 1995, COMPREHENSIVE ORGANO, V12
[8]  
JOHNSON RA, 1993, CAT ASYMMETRIC SYNTH
[9]   CATALYTIC ASYMMETRIC OXIDATIONS USING OPTICALLY-ACTIVE (SALEN)MANGANESE(III) COMPLEXES AS CATALYSTS [J].
KATSUKI, T .
COORDINATION CHEMISTRY REVIEWS, 1995, 140 :189-214
[10]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976