title: Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners.
abstract: An unexpected dichotomy was observed in the Ru-catalyzed asymmetric transfer hydrogenation of acyl phosphonates: reduction proceeded from the opposite face relative to that observed in the analogous reduction of α-keto esters. The first highly selective catalytic hydrogenation of acyl phosphonates was utilized in the dynamic kinetic resolution of α-aryl acyl phosphonates, providing β-stereogenic α-hydroxy phosphonic acid derivatives.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: Michael T
authors.initials: MT
authors.lastname: Corbett
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D000215:Acylation; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007659:Ketones; D008024:Ligands; D063065:Organophosphonates; D012428:Ruthenium