Phototriggered Generation of Ynol Ethers and Their Rearrangement to Ketenes.

Autor:	Mogami S; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Baba M; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Furuyama T; Nanomaterial Research Institute, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Kunishima M; Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 minatojima, Chuo-ku, Kobe 650-8586, Japan., Mishiro K; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.; Institute for Frontier Science Initiative, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2024 Aug 02; Vol. 89 (15), pp. 10709-10718. Date of Electronic Publication: 2024 Jul 16.
DOI:	10.1021/acs.joc.4c00947
Abstrakt:	This study developed reactions for the phototriggered generation of reactive ynol ethers using alkoxycyclopropenones. The resulting ynol ethers underwent rearrangement to ketenes, which subsequently participated in cycloaddition with alkynes and the acylation of amines. The alkoxy groups in the ynol ethers significantly influenced on the reactivity toward their rearrangement to ketenes. Reasonable transition state structures for the rearrangement reaction were found through density functional theory calculations, and the reactivity of the ynol ethers could be predicted by these calculations.
Databáze:	MEDLINE
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