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Visible-Light-Promoted α-Benzylation of N-Phenyl α-Amino Acids to α-Amino Phenylpropanoids

Lin Wang, Kang Li, Tian Ye, Lei Huang, Huilan Wu, Jingxuan Zhang, Hongqi Xie, Yisong Liu, Jianguo Zeng* and Pi Cheng*

*Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha, Hunan 410128, China, Email: zengjianguohunau.edu.cn, pichenghunau.edu.cn

L. Wang, K. Li, T. Ye, L. Huang, H. Wu, J. Zhang, H. Xie, Y. Liu, J. Zeng, P. Cheng, J. Org. Chem., 2023, 88, 11924-11934.

DOI: 10.1021/acs.joc.3c01196


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Abstract

Blue light mediates an α-C-H benzylation of readily available N-phenyl glycine ester with benzyl oxalates as a coupling partner under mild conditions to provide α-amino phenylpropanoids in good yields. The utility of this methodology is underlined by its application to the late-state modification of natural products.


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proposed mechanism



Key Words

α-Amino Acids, Benzylation, Photochemistry


ID: J42-Y2023