Journal: The Journal of organic chemistry
Article Title: Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated ?-Bromoenones with Amino Alcohols.
PMID/MRN: 27656759
Publication Date: 2016-Oct-21
Abstract:
A highly efficient method for the selective synthesis of trifluoromethylated morpholines (4-oxa-1-azabicyclo[4.1.0]heptanes) and so far unknown 1,4-oxazepanes (2,8-dioxa-5-azabicyclo[5.1.0]octanes) based on a domino reaction of fluorinated ?-bromoenones with ?-amino alcohols was elaborated. The assembly of both heterocyclic systems is initiated by an aza-Michael reaction followed by intramolecular cyclization. The conditions for total control of selectivity of the reaction were found.