CHROMIUM CATALYZED ASYMMETRIC ALKENE EPOXIDATION - GREATER SELECTIVITY FOR AN E-ALKENE VERSUS ITS Z-ISOMER

被引:76
作者
BOUSQUET, C [1 ]
GILHEANY, DG [1 ]
机构
[1] UNIV COLL DUBLIN,DEPT CHEM,DUBLIN 4,IRELAND
关键词
D O I
10.1016/0040-4039(95)01577-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
E-beta-methylstyrene can be asymmetrically epoxidised stoichiometrically with up to 83% ee and catalytically with up to 77% ee by chiral chromium complexes in the presence of phosphine oxides, DMSO or DMF. In all cases the analogous reaction with Z-beta-methylstyrene gives lower ee.
引用
收藏
页码:7739 / 7742
页数:4
相关论文
共 30 条
[11]  
IRIE R, 1991, SYNLETT, P265
[12]  
Jacobsen E.N., 1993, CATALYTIC ASYMMETRIC, P159
[13]   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
[14]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970
[15]  
JOHNSON RA, 1993, CATALYTIC ASYMMETRIC, P103
[16]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[17]   HIGHLY ENANTIOSELECTIVE RING-OPENING OF EPOXIDES CATALYZED BY (SALEN)CR(III) COMPLEXES [J].
MARTINEZ, LE ;
LEIGHTON, JL ;
CARSTEN, DH ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5897-5898
[18]   SODIUM-HYPOCHLORITE - A CONVENIENT OXYGEN SOURCE FOR OLEFIN EPOXIDATION CATALYZED BY (PORPHYRINATO)MANGANESE COMPLEXES [J].
MEUNIER, B ;
GUILMET, E ;
DECARVALHO, ME ;
POILBLANC, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6668-6676
[19]   ASYMMETRIC OXIDATION OF SULFIDES TO SULFOXIDES BY ORGANIC HYDROPEROXIDES WITH OPTICALLY-ACTIVE SCHIFF-BASE OXOVANADIUM(IV) CATALYSTS [J].
NAKAJIMA, K ;
KOJIMA, M ;
FUJITA, J .
CHEMISTRY LETTERS, 1986, (09) :1483-1486
[20]  
NISHINAGA A, 1988, TETRAHEDRON LETT, P6309