Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
Julia A. Kalow, Dana E. Schmitt and Abigail G. Doyle*
*Department of Chemistry, Princeton University, Princeton,
New Jersey 08544, United States, Email: agdoyle
princeton.edu
J. A. Kalow, D. E. Schmitt, A. G. Doyle, J. Org. Chem., 2012, 77, 4177-4183.
DOI: 10.1021/jo300433a
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Abstract
In situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol in the presence of a Lewis base catalyst enables the hydrofluorination of aziridines to provide β-fluoroamines. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.
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Key Words
ID: J42-Y2012-1250
