Asymmetric electrophilic Amination of various carbon nucleophiles with enantiomerically pure chiral N-H oxaziridines derived from camphor and fenchone

P. C. B. Bulman Page, C. Limousin, V. L. Murrell

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

The first two stable enantiomerically pure chiral N-H oxaziridines, derived from camphor and fenchone, are shown to act as electrophilic sources of nitrogen upon reaction with various carbon nucleophiles. Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters, malonates, and nitriles are used as nucleophiles. One of the ester or nitrile units in the substrate usually undergoes hydrolysis; a cyclic mechanism is proposed to account for this observation.
Original languageEnglish
Pages (from-to)7787-7796
Number of pages10
JournalJournal of Organic Chemistry
Volume67
Issue number22
DOIs
Publication statusPublished - 2002

Keywords

  • ENANTIOSELECTIVE AMINATION
  • SULFIDES
  • REAGENTS
  • AMINO-ACID-DERIVATIVES
  • GENERAL-APPROACH
  • 1-OXIDES
  • BETA-HYDROXYESTERS
  • ALPHA-HYDRAZINO ACIDS
  • NITROGEN
  • 3-DITHIANE
  • ALKYLHYDROXYLAMINES
  • 2-ACYL-1

Cite this