Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α‑Bromoenones with Amino Alcohols

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 α-bromoenones with β-amino alcohols was elaborated. The as...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-10, Vol.81 (20), p.10029-10034
Main Authors: Rulev, Alexander Yu, Romanov, Alexey R, Kondrashov, Evgeniy V, Ushakov, Igor A, Vashchenko, Alexander V, Muzalevskiy, Vasiliy M, Nenajdenko, Valentine G
Format: Article
Language:English
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Summary: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 α-bromoenones with β-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01927