Sulphur ylide-mediated stereoselective synthesis of a stable ferrocenyl epoxide

Monica Catasus, Albert Moyano, VK Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

26 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3475-3479
Number of pages5
JournalTetrahedron Letters
Volume43
Issue number19
Publication statusPublished - 6 May 2002

Keywords

  • asymmetric synthesis
  • epoxides
  • ferrocenes
  • sulphur ylides
  • CATALYTIC ASYMMETRIC EPOXIDATION
  • SULFUR YLIDES
  • SYNTHETICALLY USEFUL
  • ALDEHYDES
  • GENERATION
  • AZIRIDINES
  • MECHANISM
  • SULFIDES
  • KETONES
  • CYCLE

Cite this