α-Fluorotropinone Immobilized on Silica:  A New Stereoselective Heterogeneous Catalyst for Epoxidation of Alkenes with Oxone

The dioxirane-mediated epoxidation of alkenes in the presence of supported alpha-fluorotropinones 5 and 9 has been evaluated. The catalysts anchored onto silica supports 5 have shown comparable activity with respect to the homogeneous counterpart 10 and good stability on recycling. In the second part of this paper the enantiomerically enriched alpha-fluorotropinone 4 was anchored onto both mesoporous MCM-41 and amorphous KG-60 silicas. The chiral-supported catalysts promoted the stereoselective epoxidation of several trans-substituted and trisubstituted alkenes with ee values up to 80% and were perfectly reusable with the same performance for at least three catalytic cycles.