Tetrahedron: Asymmetry

Enzyme-catalyzed preparation of methyl (R)-N-(2, 6-dimethylphenyl) alaninate: a key intermediate for (R)-metalaxyl

OJ Park, SH Lee, TY Park, SW Lee, KH Cho

Index: Park, Oh-Jin; Lee, Sang-Hyun; Park, Tae-Yoon; Lee, Sang-Who; Cho, Koon-Ho Tetrahedron Asymmetry, 2005 , vol. 16, # 6 p. 1221 - 1225

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Citation Number: 20

Abstract

A biocatalytic approach for the production of (R)-metalaxyl, mefenoxam, has been developed. A practical synthesis of methyl (R)-N-(2, 6-dimethylphenyl) alaninate, a key intermediate for (R)-metalaxyl, has been developed by the use of lipase-catalyzed hydrolytic kinetic resolution and chemical racemization of the remaining ester. At high concentrations in aqueous media (300g/L) lipases were stable and gave moderate to good conversions ...