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
[1]   OPTICALLY-ACTIVE COMPLEXES OF SCHIFF-BASES .6. PALLADIUM (II) AND PLATINUM (II) COMPLEXES WITH QUADRIDENTATE SCHIFF-BASES OF SALICYLALDEHYDE [J].
CESAROTTI, E ;
PASINI, A ;
UGO, R .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1981, (11) :2147-2152
[2]   EFFECT OF CHIRAL QUATERNARY AMMONIUM-SALTS ON (SALEN)MN-CATALYZED EPOXIDATION OF CIS-OLEFINS - A HIGHLY ENANTIOSELECTIVE, CATALYTIC ROUTE TO TRANS-EPOXIDES [J].
CHANG, SB ;
GALVIN, JM ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6937-6938
[3]   REGIOSELECTIVE AND ENANTIOSELECTIVE EPOXIDATION CATALYZED BY METALLOPORPHYRINS [J].
COLLMAN, JP ;
ZHANG, XM ;
LEE, VJ ;
UFFELMAN, ES ;
BRAUMAN, JI .
SCIENCE, 1993, 261 (5127) :1404-1411
[4]  
GILHEANY D, UNPUB
[5]   COORDINATION OF STYRENE OXIDE TO A STERICALLY HINDERED RUTHENIUM(II) PORPHYRIN [J].
GROVES, JT ;
HAN, YZ ;
VANENGEN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :436-437
[6]   CATALYTIC ASYMMETRIC EPOXIDATIONS WITH CHIRAL IRON PORPHYRINS [J].
GROVES, JT ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5791-5796
[7]   HYDROXYLATION AND EPOXIDATION CATALYZED BY IRON-PORPHINE COMPLEXES - OXYGEN-TRANSFER FROM IODOSYLBENZENE [J].
GROVES, JT ;
NEMO, TE ;
MYERS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :1032-1033
[8]  
HAMADA T, 1994, SYNLETT, P479
[9]   RATIONAL DESIGN OF MN-SALEN EPOXIDATION CATALYSTS - PRELIMINARY-RESULTS [J].
HOSOYA, N ;
HATAYAMA, A ;
IRIE, R ;
SASAKI, H ;
KATSUKI, T .
TETRAHEDRON, 1994, 50 (15) :4311-4322
[10]   CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS [J].
IRIE, R ;
NODA, K ;
ITO, Y ;
MATSUMOTO, N ;
KATSUKI, T .
TETRAHEDRON LETTERS, 1990, 31 (50) :7345-7348