Brønsted Acid-Catalyzed Cascade Ring-Opening/Cyclization of 3-Ethoxy Cyclobutanones to Access 2,8-Dioxabicyclo[3.3.1]nonane Derivatives.

A cascade ring opening of 3-ethoxy cyclobutanones followed by a double cyclization strategy has been developed via Brønsted acid catalysis. A range of 2,8-dioxabicyclo[3.3.1]nonanes are obtained from various substituted naphthols in a one-pot and open flux manner. Additionally, a 15-membered macrocycle has been synthesized by ring closing metathesis as a synthetic application.

Merging Two Strained Carbocycles: Lewis Acid Catalyzed Remote Site-Selective Friedel-Crafts Alkylation of in Situ Generated ß-Naphthol.

Lewis acid catalyzed tandem activation of the two smallest carbocycles, 3-ethoxy cyclobutanones, and donor-acceptor cyclopropanes has been demonstrated. The diphenyl-substituted 3-ethoxy cyclobutanone rearranges itself by intramolecular cyclization for the in situ generation of 1-phenyl 2-naphthol, which further undergoes remote site-selective Friedel-Crafts alkylation with donor-acceptor cyclopropane to synthesize a series of γ-naphthyl butyric acid derivatives. Further control experiments for mechanistic investigations and synthetic applications have also been carried out.