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Synthesis and Application of Enantioenriched Functionalized α-Tetrasubstituted α-Amino Acids from Biocatalytic Desymmetrization of Prochiral α-Aminomalonamides

Li-Bing Zhang, De-Xian Wang, Liang Zhao and Mei-Xiang Wang*

*Department of Chemistry, Tsinghua University, Beijing 100084, China, Email: wangmxmail.tsinghua.edu.cn

L.-B. Zhang, D.-X. Wang, L. Zhao, M.-X. Wang, J. Org. Chem., 2012, 77, 5584-5591.

DOI: 10.1021/jo3007122 (free Supporting Information)


Abstract

Rhodococcus erythropolis AJ270, an amidase-containing microbial whole cell catalyst, enables a highly efficient and enantioselective hydrolytic desymmetrization of a number of prochiral α-substituted α-aminomalonamides in neutral phosphate buffer at 30C to afford functionalized α-tetrasubstituted α-amino acids in very good chemical yields and high ee.

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Key Words

Hydrolysis of amides


ID: J42-Y2012-2120