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通过1,4-二炔-3-醇与酸酐的串联反应构建全取代环丁烷

Construction of Fully Substituted Cyclobutanes by Tandem Reaction of 1,4-Diyn-3-ols and Anhydrides.

作者信息

Guo Ziyi, Yin Yue, Xu Xiao-Cong, Liu Chang-Qing, Zhang Jitan, Xie Meihua

机构信息

Key Laboratory of Functional Molecular Solids (Ministry of Education), Anhui Key Laboratory of Molecular Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.

出版信息

J Org Chem. 2023 Jul 7;88(13):9488-9495. doi: 10.1021/acs.joc.3c00530. Epub 2023 Jun 20.

DOI:10.1021/acs.joc.3c00530
PMID:37338541
Abstract

A concise and efficient synthesis of fully substituted cyclobutane derivatives from 1,4-diyn-3-ols and anhydrides was developed. Mechanistic studies indicated that a tandem esterification, isomerization to give allenyl ester, and homointermolecular [2+2] cycloaddition might be involved. The features of this protocol are its operational practicality, mild reaction conditions, and high regio- and stereoselectivity, and it is a readily accessible gram-scale synthesis.

摘要

开发了一种由1,4-二炔-3-醇和酸酐简洁高效地合成全取代环丁烷衍生物的方法。机理研究表明,可能涉及串联酯化、异构化生成烯丙基酯以及分子内[2+2]环加成反应。该方法的特点是操作实用性强、反应条件温和、区域和立体选择性高,并且是一种易于实现克级规模的合成方法。

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