Several chiral diastereoisomerically pure epoxy alcohols were prepared dias
tereoselectively in high yields after epoxidation of allyl and homoallyl al
cohols containing the 1R-fenchone skeleton with VO(acac)(2)/t-butyl hydrope
roxide. The configurations of some of the new chiral compounds were determi
ned by NMR methods. An interesting rearrangement reaction of an epoxy alcoh
ol to an olefinic diol catalyzed by V5+ ions was observed. (C) 1999 Elsevie
r Science Ltd. All rights reserved.