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1-酰基-2-乙烯基环丙烷重排为环庚-4-烯酮的科普重排反应

Cope Rearrangement of 1-Acyl-2-vinylcyclopropanes to Cyclohept-4-Enones.

作者信息

Wei Yinhe, Wang Gang, Zhang Zhiguo, Li Mengjuan, Ma Nana, Wu Hao, Zhang Guisheng

机构信息

Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China.

出版信息

J Org Chem. 2024 Jan 19;89(2):1127-1139. doi: 10.1021/acs.joc.3c02319. Epub 2024 Jan 2.

Abstract

Cycloheptenones are widespread in natural products and bioactive molecules. An efficient and convenient NaH-mediated Cope Rearrangement of doubly activated vinylcyclopropanes is reported for the synthesis of cyclohepten-4-ones. These flexible intramolecular reactions were applicable to a wide range of substrates and could be performed on gram scale. The derivatization of the product leads to short and highly efficient synthesis of some useful functional molecules.

摘要

环庚烯酮广泛存在于天然产物和生物活性分子中。本文报道了一种高效便捷的由氢化钠介导的双活化乙烯基环丙烷的科普重排反应,用于合成环庚烯 -4- 酮。这些灵活的分子内反应适用于多种底物,并且可以在克级规模上进行。产物的衍生化能够实现一些有用功能分子的简短且高效的合成。

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