title: Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.
abstract: The dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α-hydroxy carboxylic acid derivatives. Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Kimberly M
authors.initials: KM
authors.lastname: Steward
authors.forename: Michael T
authors.initials: MT
authors.lastname: Corbett
authors.forename: C Guy
authors.initials: CG
authors.lastname: Goodman
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D004952:Esters / Q000737:chemistry*; D006016:Glycolates / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D004952:Esters; D006016:Glycolates; D007659:Ketones; C031149:glycolic acid