Herschel Mukherjee, C. Martínez
Jul 27, 2011
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0
Influential Citations
21
Citations
Journal
ACS Catalysis
Abstract
In this work, we utilized commercial lipases (from Thermomyces lanuginosa, Rhizopus delemar, and Mucor miehei) as biocatalysts for the efficient synthesis of precursors of β-substituted-γ-amino acids. This biocatalytic route provides a practical and efficient synthesis of a wide range of optically active compounds by accepting a number of aliphatic and aromatic 3-substituted-3-cyano-2-(ethoxycarbonyl)propanoic acid ethyl esters (2) without compromising enantioselectivity or yields. The resolution step allows for the nearly quantitative recovery of the unreacted enantiomer of R-(2) as well as the newly formed 3-substituted-3-cyano-2-(ethoxycarbonyl)propanoic acid (3) in high enantio and diastereoselectivity. The use of a facile thermal decarboxylation of (3) in aqueous solution to produce 3-substituted-3-cyanopropanoic acid ethyl esters (4) enable us to prepare a wide range of optically active precursors of β-Substituted-γ-Amino Acids.