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. (C) 2002 Elsevier Science Ltd. All rights reserved.
|Number of pages||5|
|Publication status||Published - 6 May 2002|
- asymmetric synthesis
- sulphur ylides
- CATALYTIC ASYMMETRIC EPOXIDATION
- SULFUR YLIDES
- SYNTHETICALLY USEFUL