1345347-22-9Relevant academic research and scientific papers
The Hydroxyalkyl Moiety As a Protecting Group for the Stereospecific Alkylation of Masked Secondary Phosphine-Boranes
Lemouzy, Sébastien,Jean, Marion,Giordano, Laurent,Hérault, Damien,Buono, Gérard
supporting information, p. 140 - 143 (2016/01/15)
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 excl
Stereospecific Synthesis of α- And β-Hydroxyalkyl P-Stereogenic Phosphine-Boranes and Functionalized Derivatives: Evidence of the P=O Activation in the BH3-Mediated Reduction
Lemouzy, Sébastien,Nguyen, Duc Hanh,Camy, Valentine,Jean, Marion,Gatineau, David,Giordano, Laurent,Naubron, Jean-Valère,Vanthuyne, Nicolas,Hérault, Damien,Buono, Gérard
, p. 15607 - 15621 (2015/11/03)
Access to hydroxy-functionalized P-chiral phosphine-boranes has become an important field in the synthesis of P-stereogenic compounds used as ligands in asymmetric catalysis. A family of optically pure α and β-hydroxyalkyl tertiary phosphine-boranes has been prepared by using a three-step procedure from readily accessible enantiopure adamantylphosphinate, obtained by semi-preparative HPLC on multigram scale. Firstly, a two-step one-pot transformation affords the enantiopure hydroxyalkyl tertiary phosphine oxides in good yields and enantioselectivities. The third step, BH3-mediated reduction, allows the formation of the desired phosphine-boranes with excellent stereospecifity. The mechanistic study of this reduction provides new evidence to elucidate the crucial role of the pendant hydroxy group and the subsequent activation of the P=O bond by the boron atom.
Lipase-mediated stereoselective transformations of chiral organophosphorus P-boranes revisited: Revision of the absolute configuration of alkoxy(hydroxymethyl)phenylphosphine P-boranes
Kwiatkowska, Malgorzata,Krasinski, Grzegorz,Cypryk, Marek,Cierpial, Tomasz,Kielbasinski, Piotr
experimental part, p. 1581 - 1590 (2011/12/15)
The lipase-promoted kinetic resolution of a series of alkoxy(hydroxymethyl) phenylphosphine P-boranes proceeded with moderate stereoselectivity to give both the unreacted substrates and their O-acetyl derivatives. The absolute configurations of the produc
