ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION OF ALLYLIC PHOSPHINE OXIDES

被引:20
作者
CLAYDEN, J [1 ]
WARREN, S [1 ]
机构
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期
关键词
D O I
10.1039/p19940002811
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
a diphenylphosphinoyl group undergo asymmetric epoxidation with excellent enantioselectivity, and can undergo kinetic resolution with good diastereoselectivity, with the diphenylphosphinoyl group exerting an anti-directing effect on the epoxidation.
引用
收藏
页码:2811 / 2823
页数:13
相关论文
共 31 条
[1]   TRANSPOSITION OF ALLYLIC ALCOHOLS CONTROLLED BY THE PH2PO GROUP - REAGENTS FOR ALPHA-HYDROXY-DIENE SYNTHESIS BY THE HORNER-WITTIG REACTION [J].
BROWN, PS ;
MCELROY, AB ;
WARREN, S .
TETRAHEDRON LETTERS, 1985, 26 (02) :249-252
[2]   THE SYNTHESIS OF (Z)-PENTA-2,4-DIEN-1-OL AND SUBSTITUTED (E)-PENTADIENOLS BY THE STEREOCHEMICALLY CONTROLLED HORNER-WITTIG REACTION [J].
BROWN, PS ;
GREEVES, N ;
MCELROY, AB ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1485-1492
[3]   ASYMMETRIC EPOXIDATIONS AND KINETIC RESOLUTIONS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES [J].
CLAYDEN, J ;
COLLINGTON, EW ;
WARREN, S .
TETRAHEDRON LETTERS, 1992, 33 (46) :7043-7046
[4]   STEREOCONTROLLED SYNTHESIS OF R OR S, E OR Z UNSATURATED ALPHA-AMINO-ACIDS BY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES [J].
CLAYDEN, J ;
COLLINGTON, EW ;
WARREN, S .
TETRAHEDRON LETTERS, 1993, 34 (08) :1327-1330
[5]   ALKENYL OXAZOLIDINONES BY STEREOSELECTIVE EPOXIDATION OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES - SYNTHESIS OF ANY ISOMER (RR, RS, SR OR SS, E OR Z) BEARING 1,4-RELATED CHIRAL CENTERS ACROSS A DOUBLE-BOND [J].
CLAYDEN, J ;
COLLINGTON, EW ;
LAMONT, RB ;
WARREN, S .
TETRAHEDRON LETTERS, 1993, 34 (13) :2203-2206
[6]   THE SYNTHESIS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES BY PALLADIUM(II)-CATALYZED ALLYLIC ACETATE TRANSPOSITION [J].
CLAYDEN, J ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :2913-2923
[7]   STEREOCHEMICAL CONTROL (E/Z AND SYN ANTI) BY THE DIPHENYLPHOSPHINOYL GROUP IN THE SYNTHESIS OF ALLYLIC ALCOHOLS BY ALLYLIC REARRANGEMENT AND BY 1,4-DIASTEREOSELECTIVE REDUCTION OF ENONES [J].
CLAYDEN, J ;
COLLINGTON, EW ;
ELLIOTT, J ;
MARTIN, SJ ;
MCELROY, AB ;
WARREN, S ;
WATERSON, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (16) :1849-1859
[8]   THE SYNTHESIS OF DELTA-HYDROXY ALLYLIC PHOSPHINE OXIDES BY PALLADIUM(II)-CATALYZED ALLYLIC TRANSPOSITION [J].
CLAYDEN, J ;
COLLINGTON, EW ;
WARREN, S .
TETRAHEDRON LETTERS, 1992, 33 (46) :7039-7042
[9]  
CLAYDEN J, 1994, IN PRESS J CHEM SOC, P1529
[10]  
Clayden J., UNPUB