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Asymmetric Transfer Hydrogenation Coupled with Dynamic Kinetic Resolution in Water: Synthesis of anti-β-Hydroxy-α-amino Acid Derivatives

Brinton Seashore-Ludlow*, François Saint-Dizier and Peter Somfai*

*Organic Chemistry, Department of Chemical Science and Engineering, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden, Email: brintonkth.se, Peter.Somfaichem.lu.se

B. Seashore-Ludlow, F. Seint-Dizier, P. Somfai, Org. Lett., 2012, 14, 6334-6337.

DOI: 10.1021/ol303115v (free Supporting Information)



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Abstract

The use of asymmetric transfer hydrogenation combined with dynamic kinetic resolution for the synthesis of β-hydroxy-α-(tert-butoxycarbonyl)amino esters in water provides amino alcohols in good yields, diastereoselectivities, and enantioselectivities. A surfactant is employed to achieve good yields due to the hydrophobic nature of both the catalyst and substrate.

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Key Words

Reduction of Carbonyl Compounds, Amino Alcohols, Formic Acid


ID: J54-Y2012-3940