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

Autor:	Gérard Buono, Valentine Camy, Duc Hanh Nguyen, Damien Hérault, Nicolas Vanthuyne, Jean-Valère Naubron, Laurent Giordano, Marion Jean, David Gatineau, Sébastien Lemouzy
Rok vydání:	2015
Předmět:	Stereochemistry Organic Chemistry Hydroxy group Enantioselective synthesis Boranes General Chemistry Boron atom Catalysis Stereocenter chemistry.chemical_compound Enantiopure drug Stereospecificity chemistry Phosphine
Zdroj:	Chemistry - A European Journal. 21:15607-15621
ISSN:	0947-6539
DOI:	10.1002/chem.201502647
Popis:	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.
Databáze:	OpenAIRE
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