title: Synthesis of fluorinated β-aminophosphonates and γ-lactams.
abstract: The functionalized polyfluorophosphorylated 1-azadienes I have been prepared by a Wittig reaction of ethyl glyoxalate and perfluorophosphorylated conjugated phosphoranes, obtained by reaction of phosphazenes and fluorinated acetylenic phosphonates. Subsequent reduction of both carbon-carbon and carbon-nitrogen double bonds of these 1-azadienes I affords the fluorine-containing β-aminophosphonates II, with the syn β-aminophosphonate being obtained as the major diastereoisomer. Base-mediated cyclocondensation of a diastereomeric mixture of aminophosphonates II leads exclusively to a new type of functionalized trans-γ-lactams III in a diastereoselective way. A computational study has also been used to explain the observed diastereoselectivity of these reactions.
authors.affiliation: Departamento de Química Orgánica I and Lascaray Research Center, Facultad de Farmacia, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Paseo de la Universidad 7, 01006 Vitoria, Spain.
authors.forename: Concepción
authors.initials: C
authors.lastname: Alonso
authors.forename: María
authors.initials: M
authors.lastname: González
authors.forename: María
authors.initials: M
authors.lastname: Fuertes
authors.forename: Gloria
authors.initials: G
authors.lastname: Rubiales
authors.forename: Jose María
authors.initials: JM
authors.lastname: Ezpeleta
authors.forename: Francisco
authors.initials: F
authors.lastname: Palacios
mesh_terms: D005461:Fluorine / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D063088:Phosphoramides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D063088:Phosphoramides; D005461:Fluorine