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Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of ?-keto esters.

ABSTRACT: The dynamic kinetic resolution of ?-keto esters via asymmetric transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse ?-substituted-?-hydroxy carboxylic acid derivatives. Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective ?-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of ?-aryl- and ?-chloro-?-keto esters.

SUBMITTER: Steward KM

PROVIDER: S-EPMC3533366 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.

Steward Kimberly M KM Corbett Michael T MT Corbett Michael T MT Goodman C Guy CG Johnson Jeffrey S JS

Journal of the American Chemical Society 20121127 49

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 ...[more]

PMID: 23186551

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