Diastereoselective Epoxidation of Cyclohexene Derivatives by Dioxiranes Generated in Situ. Importance of Steric and Field Effects.
In this paper, diastereoselective epoxidation of substituted cyclohexenes (substrates 1-7) by dioxiranes generated in situ from ketones and Oxone was systematically investigated. The results revealed that the diastereoselectivity was determined by the steric and field effects of both dioxiranes and substrates, and high diastereoselectivity can be achieved by tuning the ketone structure. Among the ketones tested, 12 and 19 gave the best diastereoselectivities.
Yang
Dan
D
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong.
Jiao
Guan-Sheng
GS
Yip
Yiu-Chung
YC
Wong
Man-Kin
MK