Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines

Lei Zhang, Jindian Duan, Gaochen Xu, Xiaojuan Ding, Yiyang Mao, Binsen Rong, Ning Zhu, Zheng Fang, Zhenjiang Li, Kai Guo

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.

Original languageEnglish
Pages (from-to)2532-2542
Number of pages11
JournalJournal of Organic Chemistry
Volume85
Issue number4
DOIs
StatePublished - 21 Feb 2020

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