Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines

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 subst...

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Veröffentlicht in:	Journal of organic chemistry 2012-04, Vol.77 (8), p.4177-4183
Hauptverfasser:	Kalow, Julia A, Schmitt, Dana E, Doyle, Abigail G
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemistry Aziridines - chemical synthesis Aziridines - chemistry Catalysis Chemistry Exact sciences and technology Halogenation Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Lewis Bases - chemistry Molecular Structure Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo300433a