Phase-Transfer-Catalyzed Oxazirid­ine-Mediated Hydroxylative Phenol and Naphthol Dearomatization

A new methodology for the dearomative ortho-hydroxylation of substituted phenolic substrates is reported. In the presence of a phase-transfer catalyst and a base, N-sulfonyloxaziridines react with phenols to give the corresponding 6-alkyl-6-hydroxycyclohexadienone products in moderate to good yields. The reaction proceeds in fair to good yields and excellent chemoselectivity for 2,6-disubstituted phenols, 1-naphthols, and 2-naphthols.