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Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur

Masato Saito, Sho Murakami, Takeshi Nanjo, Yusuke Kobayashi and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

M. Saito, S. Murakami, T. Nanjo, Y. Kobayashi, Y. Takemoto, J. Am. Chem. Soc., 2020, 142, 8130-8135.

DOI: 10.1021/jacs.0c03256 (free Supporting Information)


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Abstract

A nucleophilic activation of elemental sulfur by thiols enables a mild and chemoselective thioacylation of amines with α-keto acids and elemental sulfur. The reaction tolerates a broad range of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties.

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Key Words

thioacylation, thionation, organocatalysis, multicomponent reactions


ID: J48-Y2020