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

Publisher: American Chemical Society Country of Publication: United States NLM ID: 7503056 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5126 (Electronic) Linking ISSN: 00027863 NLM ISO Abbreviation: J Am Chem Soc Subsets: MEDLINE

Publication: Washington, DC : American Chemical Society
Original Publication: Easton, Pa. [etc.]

Thermodynamics*; Esters/*chemistry ; Glycolates/*chemical synthesis ; Ketones/*chemistry; Glycolates/chemistry ; Hydrogenation ; Kinetics ; Molecular Conformation ; Stereoisomerism

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.

Erratum in: J Am Chem Soc. 2015 Mar 25;137(11):3991. (PMID: 25751640)

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R01 GM084927 United States GM NIGMS NIH HHS

0 (Esters)
0 (Glycolates)
0 (Ketones)
0WT12SX38S (glycolic acid)

Date Created: 20121129 Date Completed: 20130605 Latest Revision: 20240514

20240514

PMC3533366

10.1021/ja3102709

23186551