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

Alexander Yu Rulev; Alexey R Romanov; Evgeniy V Kondrashov; Igor A Ushakov; Alexander V Vashchenko; Vasiliy M Muzalevskiy; Valentine G Nenajdenko

doi:10.1021/acs.joc.6b01927

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

J Org Chem. 2016 Oct 21;81(20):10029-10034. doi: 10.1021/acs.joc.6b01927. Epub 2016 Oct 4.

Authors

Alexander Yu Rulev¹, Alexey R Romanov¹, Evgeniy V Kondrashov¹, Igor A Ushakov¹, Alexander V Vashchenko¹, Vasiliy M Muzalevskiy², Valentine G Nenajdenko²

Affiliations

¹ A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
² Department of Chemistry, Lomonosov Moscow State University , Moscow 119899, Russia.

PMID: 27656759
DOI: 10.1021/acs.joc.6b01927

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 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.

Publication types

Research Support, Non-U.S. Gov't