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Asymmetric Synthesis of anti-β-Amino-α-Hydroxy Esters via Dynamic Kinetic Resolution of β-Amino-α-Keto Esters

C. Guy Goodman, Dung T. Do and Jeffrey S. Johnson*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, 27599-3250, United States, Email: jsjunc.edu

C. G. Goodman, D. T. Do, J. S. Johnson, Org. Lett., 2013, 15, 2446-2449.

DOI: 10.1021/ol4009206 (free Supporting Information)



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Abstract

α-Keto esters can be 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 enantioenriched anti-α-hydroxy-β-amino acid derivatives in high diastereo- and enantioselectivity.

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Key Words

Oxone, Oxidation, Reduction, Boc-protected amines


ID: J54-Y2013