Dearomative Cyclopropanation of Naphthols via Cyclopropene Ring‐Opening
Rachel J. Baker, Justin Ching, Teh Ren Hou, Ivan Franzoni, Mark Lautens
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.
Topics & Concepts
CyclopropeneCyclopropanationCyclopropaneChemoselectivityRing (chemistry)ChemistryCatalysisRhodiumMoleculeCombinatorial chemistryComputational chemistryStereochemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsSynthetic Organic Chemistry Methods