A Regioselective [3 + 2] Cycloaddition of Alkynols and Ketones To Access Diverse 1,3-Dioxolane Scaffolds
Ganesh Kumar Dhandabani1,2, Palaniraja Jeyakannu1, Chia-Ling Shih1,2
1Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shih-Chuan First Road, Sanmin District, Kaohsiung City, 807, Taiwan.
Abstract:
This study presents a stepwise exoselective [3 + 2] cycloaddition reaction of alkynols with ketones, leading to the synthesis of 4-methylene-1,3-dioxolane derivatives. Remarkably, without any Thorpe-Ingold induced effect, the cyclization reaction was demonstrated with complete regio- and chemoselectivity, which was solely promoted by cesium carbonate. A wide range of unactivated ketones are viable under these mild reaction conditions, and both primary and tertiary alkynols are compatible with these cyclization reactions. We have prepared a diverse array of highly dense exomethylene 1,3-dioxolane rings demonstrating a remarkable tolerance for various functional groups.
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