Abstract
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.
| Translated title of the contribution | 'Sulphur ylide-mediated stereoselective synthesis of a stable ferrocenyl epoxide' |
|---|---|
| Original language | English |
| Pages (from-to) | 3475-3479 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 43 |
| Issue number | 19 |
| Publication status | Published - 6 May 2002 |
Keywords
- asymmetric synthesis
- epoxides
- ferrocenes
- sulphur ylides
- CATALYTIC ASYMMETRIC EPOXIDATION
- SULFUR YLIDES
- SYNTHETICALLY USEFUL
- ALDEHYDES
- GENERATION
- AZIRIDINES
- MECHANISM
- SULFIDES
- KETONES
- CYCLE