Oxygen transfer reactions from an oxaziridinium tetrafluoroborate salt to olefins

被引:64
作者
Lusinchi, X [1 ]
Hanquet, G [1 ]
机构
[1] ECOLE CHIM POLYMERES & MAT,CNRS URA 466,F-67008 STRASBOURG,FRANCE
关键词
D O I
10.1016/S0040-4020(97)00890-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxaziridinium 5 efficiently epoxidises olefins. It reacts as an electrophilic reagent and does not transfer its oxygen to deactivated double-bonds or carbonyl functions. Epoxidation of cyclic allylic acetates shows a remarkable diastereoselectivity leading to the syn isomer. We propose that the epoxidation reaction proceeds through a one-step process. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:13727 / 13738
页数:12
相关论文
共 52 条
[1]   DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].
ADAM, W ;
HADJIARAPOGLOU, L ;
SMERZ, A .
CHEMISCHE BERICHTE, 1991, 124 (01) :227-232
[3]   SOLVENT EFFECTS IN THE DIMETHYLDIOXIRANE OXIDATION OF ALLYLIC ALCOHOLS - EVIDENCE FOR HYDROGEN-BONDING IN THE DIPOLAR TRANSITION-STATE OF OXYGEN-TRANSFER [J].
ADAM, W ;
SMERZ, AK .
TETRAHEDRON, 1995, 51 (47) :13039-13044
[4]   OXIDATION OF ALLYLIC ALCOHOLS BY DIMETHYLDIOXIRANE - COMPETITION REACTION BETWEEN EPOXIDATION AND C-H INSERTION [J].
ADAM, W ;
PRECHTL, F ;
RICHTER, MJ ;
SMERZ, AK .
TETRAHEDRON LETTERS, 1993, 34 (52) :8427-8430
[5]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[6]   REACTION OF CYANOGEN AZIDE WITH NORBORNADIENE [J].
ANASTASSIOU, AG .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04) :1131-+
[7]   ANODIC-OXIDATION OF ORGANIC-COMPOUNDS .22. ANODIC HYDROXYLATION AND ACETAMIDATION OF CONJUGATED DIENES [J].
BALTES, H ;
STORK, L ;
SCHAFER, HJ .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (03) :807-817
[8]  
BARET P, 1967, B SOC CHIM FR, V4, P4735
[9]  
BARTON DHR, 1979, COMPREHENSIVE ORGANI, V1, P861
[10]  
Berti G., 1973, Topics in Stereochemistry, V7, P93