title: An efficient entry to optically active anti- and syn-beta-amino-alpha-trifluoromethyl alcohols.
abstract: The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: Laia
authors.initials: L
authors.lastname: Albert
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.forename: Juan F
authors.initials: JF
authors.lastname: Sanz-Cervera
authors.forename: Amparo
authors.initials: A
authors.lastname: Asensio