Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring-Opening.

Angew Chem Int Ed Engl

Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada.

Published: February 2022


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Article Abstract

The dearomatization of 2-naphthols represents a simple method for the construction of complex 3D structures from simple planar starting materials. We describe a cyclopropanation of 2-naphthols that proceeds via cyclopropene ring-opening using rhodium and acid catalysis under mild conditions. The vinyl cyclopropane molecules were formed with high chemoselectivity and scalability, which could be further functionalized at different sites. Both computational and experimental evidence were used to elucidate the reaction mechanism.

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http://dx.doi.org/10.1002/anie.202116171DOI Listing

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