Copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with vinyl cations

Ze-Shu Wang; Hao-Jin Xu; Yang-Bo Chen; Long-Wu Ye; Bo Zhou; Peng-Cheng Qian

doi:10.1039/d3cc04817a

Copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with vinyl cations

Chem Commun (Camb). 2023 Dec 14;59(100):14831-14834. doi: 10.1039/d3cc04817a.

Authors

Ze-Shu Wang^{1

2}, Hao-Jin Xu², Yang-Bo Chen², Long-Wu Ye^{2

3}, Bo Zhou², Peng-Cheng Qian^{1

2}

Affiliations

¹ Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. qpc@wzu.edu.cn.
² Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 38013471
DOI: 10.1039/d3cc04817a

Abstract

The enantioselective transformation of easily accessible 1,2-diketones represents a quick pathway towards enantioenriched molecules. Herein, we disclose a copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with vinyl cations, enabling the efficient and atom-economical construction of axially chiral arylpyrroles bearing 1,3-dioxole moieties with good to excellent enantioselectivities under mild reaction conditions. Importantly, this methodology constitutes the first enantioselective formal [4+1] annulation of 1,2-diketones.