title: Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.
abstract: A method for the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivatives by enantioconvergent reduction of the corresponding racemic α-keto esters is presented. The requisite α-keto esters are prepared via Mannich addition of ethyl diazoacetate to imines followed by oxidation of the diazo group with Oxone. Implementation of a recently developed dynamic kinetic resolution of β-substituted-α-keto esters via Ru(II)-catalyzed asymmetric transfer hydrogenation provides the title motif in routinely high diastereo- and enantioselectivity.
authors: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina, 27599-3250, United States.
authors: C Guy
authors: CG
authors: Goodman
authors: Dung T
authors: DT
authors: Do
authors: Jeffrey S
authors: JS
authors: Johnson
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D007651:Keto Acids / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D004952:Esters; D007651:Keto Acids; D012428:Ruthenium
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