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; Pi Cheng

doi:10.1021/acs.joc.3c01196

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

J Org Chem. 2023 Aug 18;88(16):11924-11934. doi: 10.1021/acs.joc.3c01196. Epub 2023 Aug 10.

Authors

Lin Wang^{1

2}, Kang Li^{1

2}, Tian Ye^{1

3}, Lei Huang^{1

3}, Huilan Wu^{1

2}, Jingxuan Zhang^{1

2}, Hongqi Xie^{1

3}, Yisong Liu^{1

3}, Jianguo Zeng^{1

3}, Pi Cheng^{1

3}

Affiliations

¹ Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha, Hunan 410128, China.
² College of Horticulture, Hunan Agricultural University, Changsha, Hunan 410128, China.
³ College of Veterinary Medicine, Hunan Agricultural University, Changsha, Hunan 410128, China.

PMID: 37560787
DOI: 10.1021/acs.joc.3c01196

Abstract

A new method for the synthesis of α-amino phenylpropanoids under blue light-emitting diode irradiation has been developed through α-C-H benzylation of readily available N-phenyl glycine ester with benzyl oxalates as a coupling partner under mild conditions. A range of N-phenyl glycine esters were successfully converted to α-amino phenylpropanoid products in moderate to good yields. The utility of this methodology is underlined by its application to the late-state modification of natural products.