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N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones
https://gifu-pu.repo.nii.ac.jp/records/14387
https://gifu-pu.repo.nii.ac.jp/records/14387c8de0c51-9c21-4bb1-9523-5d2868849498
| Item type | 研究室原著論文(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2022-03-02 | |||||
| タイトル | ||||||
| タイトル | N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones | |||||
| タイトル | ||||||
| タイトル | N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones | |||||
| 言語 | en | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 抄録 | ||||||
| 値 | The stereoselective synthesis of cis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) I (R = 4-iodophenyl, cyclopropyl, pyridin-3-yl, etc.) from O-alkyl hydroxamic acids RC(O)NHOCH3 in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature The reaction tolerated various O-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuterated cis-β-N-MeO-amide-VBXs, e.g., II, were also synthesized using deuterium oxide as the deuterium source. Valine-derived cis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derived cis-enamides, e.g., III, without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio. | |||||
| 書誌情報 |
en : Organic & Biomolecular Chemistry 巻 19, 号 11, p. 2442-2447, 発行日 2021 |
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