Epoxidation of chiral electron-deficient alkenes with basic heterogeneous catalysts

Two chiral alkenes derived from d-glyceraldehyde, bearing different electron-withdrawing groups, were transformed into their corresponding epoxides using two different heterogeneous systems, TBHP+KF/alumina and H2O2+hydrotalcite. The system TBHP+KF/alumina was more efficient and selective, leading up to 50% diastereomeric excess (de) and has the advantage of an easy work-up. The system H2O2+hydrotalcite is an efficient, simple and completely selective method for the nitrile hydrolysis in the presence of other hydrolyzable groups, such as epoxide or ester.This work was made possible by the generous financial support of the C.I.C.Y.T. (Project MAT99-1176).Peer reviewe