WANG Fang, ZHANG Yue-cheng, RAN Wei-jin, ZHAO Ji-quan^*

School of Chemical Engineering, Hebei University of Technology, Tianjin 300130, China

Abstract: Several chiral bispidine derivatives were synthesized from N-alkyl-4-piperidone and used as ligands in the asymmetric epoxidation of prochiral olefins catalyzed by methyltrioxorhenium (MTO) with urea-hydrogen peroxide (UHP) as oxidant in methanol. The effects of reaction parameters on the performance of catalyst were studied. The results revealed the chiral bispidine derivatives can decrease the catalytic activity of MTO, but increase of the selectivity of the epoxides. Meantime, all the chiral compounds showed low chiral induction in the asymmetric epoxidation of prochiral olefins. The enantio excesses (ee) are only in the range of 4% to 11%. The reasons leading to the low ee were discussed.

Key words: chiral bispidine derivatives, methyltrioxorhenium, olefins, asymmetric epoxidation, styrene

E-mail: zhaojq@hebut.edu.cn

Journal of Molecular Catalysis, Vol. 24, Issue 3, 2010, 240-246