Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents

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公開日
2019-08-06
資源種別
journal article
権利情報
  • This is the peer reviewed version of the following article: [Masato Saito, Yusuke Kobayashi, Yoshiji Takemoto. Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents. Chemistry - A European, 25(44), 10314-10318], which has been published in final form at https://doi.org/10.1002/chem.201902699. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
  • The full-text file will be made open to the public on 05 August 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
  • This is not the published version. Please cite only the published version.
  • この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI
  • 10.1002/chem.201902699
公開者
Wiley

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説明

The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex molecules such as peptides or steroids were possible. A mild and efficient method for the synthesis of various iodonium ylides was established. DFT calculations suggested that the halogen bonding between a thioamide and iodonium ylide was important in this chemoselective coupling reaction. The potential use of enaminones conjugated with pharmaceuticals as prodrugs was also demonstrated.

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