Synthesis of new ferrocenyl-substituted aziridines via the Gabriel-Cromwell reaction

Dogan O., ZEYTİNCİ S., BULUT A.

SYNTHETIC COMMUNICATIONS, vol.35, no.8, pp.1067-1076, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 35 Issue: 8
  • Publication Date: 2005
  • Doi Number: 10.1081/scc-200054207
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1067-1076
  • Keywords: alpha-bromoacryloyferrocene, alpha-bromocrotonoylferrocene, aziridines, ferrocenylenones, Gabriel-Cromwell method, 1,3-DIPOLAR CYCLOADDITIONS, ASYMMETRIC-SYNTHESIS, AZOMETHINE YLIDES, CHIRAL AZIRIDINES, ACID-DERIVATIVES, AMINO-ACIDS, ALPHA-AMINO, AZIRIDINE-2-CARBOXYLATES, AUXILIARY, EFFICIENT
  • Middle East Technical University Affiliated: Yes

Abstract

The Gabriel -Cromwell method is applied successfully in the synthesis of ferrocenyl-substituted aziridines. Acryloyl- and crotonoy1ferrocenes are brominated first and then reacted with benzylamine, diisopropylamine, and furfurylamine in the presence of triethylamine. The aziridines are obtained in more than 90% isolated yields.