Sulphur ylide-mediated stereoselective synthesis of a stable ferrocenyl epoxide

The sulphur ylide-mediated synthesis of epoxides from aldehydes with in situ generation of diazocompounds has been used to prepare, for the first time, a stable epoxyferrocene, trans-2-phenyl-3-ferrocenyloxirane 3. By means of a chiral sulphide, oxirane 3 has been obtained with high enantioselectivity. Nucleophilic opening of the epoxide ring in 3 by azide anion takes place regioselectively at the position adjacent to the ferrocene moiety and with retention of configuration.