Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of alpha-Keto Esters

作者:Steward Kimberly M; Corbett Michael T; Goodman C Guy; Johnson Jeffrey S*
来源:Journal of the American Chemical Society, 2012, 134(49): 20197-20206.
DOI:10.1021/ja3102709

摘要

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

  • 出版日期2012-12-12