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Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

Long Hu, Silin Xu, Zhenguang Zhao, Yang Yang, Zhiyuan Peng, Ming Yang, Changliu Wang and Junfeng Zhao*

*Key Laboratory of Chemical Biology of Jiangxi Province, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China, Email: zhaojfjxnu.edu.cn

L. Hu, S. Xu, Z. Zhao, Y. Yang, Z. Peng, M. Yang, C. Wang, J. Zhao, J. Am. Chem. Soc., 2016, 138, 13135-13138.

DOI: 10.1021/jacs.6b07230 (free Supporting Information)


Abstract

Ynamides as novel coupling reagents enable a highly efficient, two-step, one-pot synthetic strategy for amides and peptides under extremely mild reaction conditions. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of -OH, -SH, -CONH2, ArNH2, and the NH of indole was observed.

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Key Words

amides


ID: J48-Y2016