title: D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides.
abstract: D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transformation in a highly selective fashion. The methodology employed consisted of three steps: diastereoselective formation of the oxazaphospholidine followed by subsequent selective cleavage of P-N and P-O bonds by reaction with two Grignard reagents. P-epimers oxazaphospholidines were prepared switching from a P(v) to a P(III) precursor, thus allowing for the synthesis of enantiomeric phosphine oxides. In addition, the chiral auxiliary could be recovered and efficiently recycled.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS-UMR CNRS 5246), Université Claude Bernard Lyon 1, Bâtiment Curien (CPE) 43, Bd du 11 Novembre 1918, 69622 Villeurbanne cedex, France. eric.framery@univ-lyon1.fr.
authors.forename: A
authors.initials: A
authors.lastname: D'Onofrio
authors.forename: L
authors.initials: L
authors.lastname: Copey
authors.forename: L
authors.initials: L
authors.lastname: Jean-Gérard
authors.forename: C
authors.initials: C
authors.lastname: Goux-Henry
authors.forename: G
authors.initials: G
authors.lastname: Pilet
authors.forename: B
authors.initials: B
authors.lastname: Andrioletti
authors.forename: E
authors.initials: E
authors.lastname: Framery