title: Domino Assembly of Trifluoromethylated N,O-Heterocycles by the Reaction of Fluorinated α-Bromoenones with Amino Alcohols.
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.
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Rulev
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
authors.forename: Alexey R
authors.initials: AR
authors.lastname: Romanov
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
authors.forename: Evgeniy V
authors.initials: EV
authors.lastname: Kondrashov
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
authors.forename: Igor A
authors.initials: IA
authors.lastname: Ushakov
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences , Irkutsk 664033, Russia.
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Vashchenko
authors.affiliation: Department of Chemistry, Lomonosov Moscow State University , Moscow 119899, Russia.
authors.forename: Vasiliy M
authors.initials: VM
authors.lastname: Muzalevskiy
authors.affiliation: Department of Chemistry, Lomonosov Moscow State University , Moscow 119899, Russia.
authors.forename: Valentine G
authors.initials: VG
authors.lastname: Nenajdenko