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Lewis acid-catalyzed diastereoselective carbofunctionalization of bicyclobutanes employing naphthols

Guin, A and Bhattacharjee, S and Harariya, MS and Biju, AT (2023) Lewis acid-catalyzed diastereoselective carbofunctionalization of bicyclobutanes employing naphthols. In: Chemical Science .

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Official URL: https://doi.org/10.1039/d3sc01373a


Traditional radical-mediated ring-opening of bicyclo[1.1.0]butanes (BCBs) for cyclobutane synthesis suffers from poor diastereoselectivity. Although few reports on BCB ring-opening via polar mechanisms are available, the Lewis acid-catalyzed diastereoselective ring-opening of BCBs using carbon nucleophiles is still underdeveloped. Herein, we report a mild and diastereoselective Bi(OTf)3-catalyzed ring-opening of BCBs employing 2-naphthols. The anticipated carbofunctionalized trisubstituted cyclobutanes were obtained via a bicoordinated bismuth complex and the products are formed in good to excellent yields with high regio- and diastereoselectivity. The scope of the reaction was further extended using electron-rich phenols and naphthylamine. The functionalization of the synthesized trisubstituted cyclobutanes shows the synthetic utility of the present method.

Item Type: Journal Article
Publication: Chemical Science
Publisher: Royal Society of Chemistry
Additional Information: The copyright for this article belongs to the Royal Society of Chemistry.
Keywords: Bismuth compounds; Catalysis; Naphthol, 2-naphthols; Bismuth complexes; Carbon nucleophiles; Cyclobutanes; Diastereoselective; Diastereoselectivities; Electron-rich phenols; Lewis Acid; Naphthylamine; Ring opening, Stereoselectivity
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 14 Jul 2023 06:17
Last Modified: 14 Jul 2023 06:17
URI: https://eprints.iisc.ac.in/id/eprint/82399

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