Phototriggered Generation of Ynol Ethers and Their Rearrangement to Ketenes

被引：0

作者：

Mogami, Shunsuke ^{[1
]}

Baba, Masanobu ^{[1
]}

Furuyama, Taniyuki ^{[2
]}

Kunishima, Munetaka ^{[3
]}

Mishiro, Kenji ^{[1
,4
]}

机构：

[1] Kanazawa Univ, Inst Med Pharmaceut & Hlth Sci, Fac Pharmaceut Sci, Kanazawa 9201192, Japan

[2] Kanazawa Univ, Nanomat Res Inst, Kanazawa 9201192, Japan

[3] Kobe Gakuin Univ, Fac Pharmaceut Sci, Kobe 6508586, Japan

[4] Kanazawa Univ, Inst Frontier Sci Initiat, Kanazawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 15期

关键词：

Amines - Density functional theory;

D O I：

10.1021/acs.joc.4c00947

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：10709 / 10718

页数：10

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