Access to Deuterated Unnatural α-Amino Acids and Peptides by Photochemical Acyl Radical Addition
Li Liu, Zikun Deng, Kun Xu*, Pengxing Jiang, Hongguang Du* and Jiajing Tan*
*Beijing University of Technology, Beijing 100124; Beijing University of Chemical Technology, Beijing 100029, China,
Email: kunxu
bjut.edu.cn, dhgmail.buct.edu.cn, tanjjmail.buct.edu.cn
L. Liu, Z. Deng, K. Xu, P. Jiang, H. Du, J. Tan, Org. Lett., 2021, 23, 5288-5293.
DOI: 10.1021/acs.orglett.1c01448
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Abstract
A visible-light-enabled, photocatalyst-free conjugate addition of 4-acyl-1,4-dihydropyridines to dehydroamino acids provides β-acyl α-amino acids and their deuterated analogues in good yields. 4-Acyl-1,4-dihydropyridines serve both as a radical reservoir and reductant. The reaction can be used for late-stage peptide modification and stereoselective synthesis of chiral oxazolidinones.
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Key Words
α-Amino Acids, Acylation, photochemistry
ID: J54-Y2021
