A Regioselective [3 + 2] Cycloaddition of Alkynols and Ketones To Access Diverse 1,3-Dioxolane Scaffolds

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 chemoselect...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-01, Vol.89 (1), p.719-724
Main Authors: Dhandabani, Ganesh Kumar, Jeyakannu, Palaniraja, Shih, Chia-Ling, Abraham, Aksa Mariyam, Senadi, Gopal Chandru, Wang, Jeh-Jeng
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01820