Sulphur ylide-mediated stereoselective synthesis of a stable ferrocenyl epoxide

✍ Scribed by Mònica Catasús; Albert Moyano; Varinder K. Aggarwal

• Book ID: 104250996
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 92 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00578-6

✦ Synopsis

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.