New optically active ruthenium porphyrin catalysts for asymmetric epoxidation of styrenes

被引:12
作者
Le Maux, P [1 ]
Lukas, M [1 ]
Simonneaux, G [1 ]
机构
[1] Univ Rennes 1, Lab Chim Organomet & Biol, UMR 6509, F-35042 Rennes, France
关键词
ruthenium porphyrins; enantioselectivity; epoxidation;
D O I
10.1016/S1381-1169(03)00408-4
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
New C-2-chiral porphyrins bearing cyclohexyl substituents at ortho position of the meso-phenyl groups have been synthesized. Their ruthenium complexes have been used as enantioselective catalysts for the epoxidation of styrene derivatives using 2,6-dichloropyridine-N-oxide as oxidant with moderate selectivity (35% e.e. with 1,2-dihydronaphtalene). (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码:95 / 103
页数:9
相关论文
共 41 条
[1]   BROMINATIVE DECARBOXYLATION OF OPTICALLY ACTIVE SILVER TRANS-1,2-CYCLOHEXANEDICARBOXYLATE [J].
APPLEQUIST, DE ;
WERNER, ND .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (01) :48-&
[2]   ASYMMETRICAL HYDROGENATION IN PRESENCE OF CHIRAL DIPHOSPHINES [J].
AVIRONVIOLET, P ;
VARAGNAT, J ;
COLLEUILLE, Y .
JOURNAL OF MOLECULAR CATALYSIS, 1979, 5 (01) :41-50
[3]   REACTIONS OF TERT-BUTYLLITHIUM WITH ALPHA,OMEGA-DIHALOALKANES - EVIDENCE FOR SINGLE-ELECTRON-TRANSFER-MEDIATED METAL-HALOGEN INTERCHANGE INVOLVING ALKYL RADICAL-HALIDE ION ADDUCTS [J].
BAILEY, WF ;
GAGNIER, RP ;
PATRICIA, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2098-2107
[4]   Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxides [J].
Berkessel, A ;
Frauenkron, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16) :2265-2266
[5]  
COLLET A, 1972, B SOC CHIM FR, P336
[6]   An efficient catalyst for asymmetric epoxidation of terminal olefins [J].
Collman, JP ;
Wang, Z ;
Straumanis, A ;
Quelquejeu, M ;
Rose, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :460-461
[7]   SYNTHESIS, CHARACTERIZATION, AND X-RAY STRUCTURE OF THE RUTHENIUM PICNIC-BASKET PORPHYRINS [J].
COLLMAN, JP ;
BRAUMAN, JI ;
FITZGERALD, JP ;
HAMPTON, PD ;
NARUTA, Y ;
SPARAPANY, JW ;
IBERS, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3477-3486
[8]   IMPROVED SYNTHESES OF THE HEXANUCLEAR CLUSTERS [RU6(CO)18]2-, [HRU6-(CO)18]-, AND H2RU6(CO)18 - X-RAY-ANALYSIS OF [HRU6(CO)18]-, - POLYNUCLEAR CARBONYL CONTAINING AN INTERSTITIAL HYDROGEN LIGAND [J].
EADY, CR ;
JACKSON, PF ;
JOHNSON, BFG ;
LEWIS, J ;
MALATESTA, MC ;
MCPARTLIN, M ;
NELSON, WJH .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1980, (03) :383-392
[9]  
EVANS RF, 1959, RECL TRAV CHIM PAY B, V78, P408
[10]   Synthesis and characterisation of a new chiral ruthenium picket-fence porphyrin and its use in chiral recognition of racemic isocyanides [J].
Galardon, E ;
Lukas, M ;
Le Maux, P ;
Simonneaux, G .
TETRAHEDRON LETTERS, 1999, 40 (14) :2753-2756