title: The Hydroxyalkyl Moiety As a Protecting Group for the Stereospecific Alkylation of Masked Secondary Phosphine-Boranes.
abstract: The synthesis of functionalized tertiary phosphine-boranes has been developed via a chemodivergent approach from readily accessible (hydroxymethyl) phosphine-boranes under mild conditions. O-Alkylation or decarbonylative P-alkylation product could be exclusively obtained. The P-alkylation reaction was found to proceed in moderate to very good yields and very high enantiospecificity (es >95%) using a variety of alkyl halides as electrophiles. The configurational stability of the sodium phosphido-borane intermediate was also investigated and allowed a deeper understanding of the reaction mechanism, furnishing secondary phosphine-boranes in moderate yield and enantiopurity.
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS. iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Lemouzy
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS. iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Jean
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS. iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Giordano
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS. iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Hérault
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS. iSm2 UMR 7313, 13397, Marseille, France.
authors.forename: Gérard
authors.initials: G
authors.lastname: Buono