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Dynamic Kinetic Resolution of α-Keto Esters via Asymmetric Transfer Hydrogenation

Kimberly M. Steward, Emily C. Gentry and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, 2799-3290, United States, Email: jsjunc.edu

K. M. Steward, E. C. Gentry, J. S. Johnson, J. Am. Chem. Soc., 2012, 134, 7329-7332.

DOI: 10.1021/ja3027136 (free Supporting Information)


Abstract

The dynamic kinetic resolution of β-aryl α-keto esters using a newly designed (arene)RuCl(monosulfonamide) transfer hydrogenation catalyst generates three contiguous stereocenters with remarkable diastereoselectivity through a reduction/lactonization sequence. The resulting enantioenriched, densely functionalized γ-butyrolactones are of high synthetic utility.

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Key Words

Stetter Reaction, γ-butyrolactones


ID: J48-Y2012-1400