Nucleophilic substitution at the internal carbon of sumanene framework with inversion of configuration

Abstract

Nucleophilic substitution at the hydroxylated internal carbon of sumanene proceeded with anisole or phenol as a nucleophile promoted by trifluoromethansulfonic acid (TfOH) to give the carbon-carbon bond products. The stereochemistry of the substitution was determined to be an inversion using an enantiopure reactant. The result indicated that the nucleophile attacked exclusively from the concave side of the bowl.