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

• 村上, 翔

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 南條, 毅

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 小林, 祐輔

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 竹本, 佳司

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto, Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

抄録

A mild and chemoselective method for the thioacylation of amines using α-keto acids and elemental sulfur has been developed. The key to the success of this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties, are tolerated under the applied reaction conditions. To demonstrate the advantages of this method compared with conventional O–S exchange reactions using Lawesson’s reagent or P2S5, thioamide moieties were introduced site-specifically into biologically active compounds.

収録刊行物

• Journal of the American Chemical Society

  Journal of the American Chemical Society 142 (18), 8130-8135, 2020-05-06

  American Chemical Society (ACS)

キーワード

• Colloid and Surface Chemistry
• Biochemistry
• General Chemistry
• Catalysis

詳細情報

• CRID: 1050285299907659392
• NII論文ID: 120006876568
• ISSN: 15205126
• ISSN: 00027863
• DOI: 10.1021/jacs.0c03256
• HANDLE: 2433/253551
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/jacs.0c03256
• 本文言語コード: en
• 資料種別: journal article
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