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Inada H, Shibuya M, Yamamoto Y. Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine. J Org Chem. 2020;85(17):11047-11059doi: 10.1021/acs.joc.0c01302.
Inada, H., Shibuya, M., & Yamamoto, Y. (2020). Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine. The Journal of organic chemistry, 85(17), 11047-11059. https://doi.org/10.1021/acs.joc.0c01302
Inada, Haruki, et al. "Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine." The Journal of organic chemistry vol. 85,17 (2020): 11047-11059. doi: https://doi.org/10.1021/acs.joc.0c01302
Inada H, Shibuya M, Yamamoto Y. Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine. J Org Chem. 2020 Sep 04;85(17):11047-11059. doi: 10.1021/acs.joc.0c01302. Epub 2020 Aug 18. PMID: 32790313.
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J Org Chem. 2020 Sep 04;85(17):11047-11059. doi: 10.1021/acs.joc.0c01302. Epub 2020 Aug 18.

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine.

The Journal of organic chemistry

Haruki Inada, Masatoshi Shibuya, Yoshihiko Yamamoto

Affiliations

  1. Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan.

PMID: 32790313 DOI: 10.1021/acs.joc.0c01302

Abstract

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

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