Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines

Julia A. Kalow, Dana E. Schmitt, Abigail Gutmann Doyle

Research output: Contribution to journalArticle

67 Scopus citations

Abstract

Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.

Original languageEnglish (US)
Pages (from-to)4177-4183
Number of pages7
JournalJournal of Organic Chemistry
Volume77
Issue number8
DOIs
StatePublished - Apr 20 2012

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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