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

Autor: Wang ZS; Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. qpc@wzu.edu.cn.; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn., Xu HJ; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn., Chen YB; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn., Ye LW; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn.; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China., Zhou B; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn., Qian PC; Institute of New Materials & Industry Technology, College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China. qpc@wzu.edu.cn.; Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. longwuye@xmu.edu.cn.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2023 Dec 14; Vol. 59 (100), pp. 14831-14834. Date of Electronic Publication: 2023 Dec 14.
DOI: 10.1039/d3cc04817a
Abstrakt: 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.
Databáze: MEDLINE