1, 3‐O‐Transposition or Trisubstituted Z‐Enol Ester? A Comparative Study of Reactions of Ynones
发布时间：2021-07-02
点击次数：
DOI码：10.1002/asia.201900315
发表刊物：Chemistry–An Asian Journal
摘要：Ynones are useful substrates for transition‐metal‐mediated synthesis. The AuI‐catalyzed 1,3‐O‐transposition is an important reaction of ynones. Recently, an efficient CuI‐catalyzed synthesis of trisubstituted Z‐enol esters via interrupting the traditional 1,3‐O‐transposition reaction of ynones was reported by Zhu's group. Herein, density functional theory studies disclosed that the hydrogen bond formed by carboxylic acid plays an important role for the reactivity and selectivity in this novel reaction. A qualitative rule was also found to explain the substituent effect in the ynone substrate, and this is consistent with experiments. The AuI‐catalyst and CuI‐catalyst were further compared to interpret the essential cause of why the AuI‐catalyst prefers the 1,3‐O‐transpostion reaction. These conclusions might be helpful for the rational design of reactions of ynones.
合写作者：Changyuan Zhang, Penggang Yin
第一作者：Tian‐Yu Sun
通讯作者：Kai Chen*, Tingting You*
学科门类：理学
一级学科：化学
文献类型：J
卷号：14
期号：11
页面范围：1941-1944
是否译文：否
发表时间：2019-06-03
收录刊物：SCI
发布期刊链接：https://onlinelibrary.wiley.com/doi/abs/10.1002/asia.201900315