Oxidative Dearomatization and Sigmatropic 1,3-Acyl Shift in Excited State: Aromatics to Embellished cis-Hydrindanes

Abstract

A stereoselective synthetic route to embellished cis-hydrindanes from simple aromatic precursors is described. Oxidative dearomatization, ring expansion, and photochemical 1,3-acyl shift are the key features of our approach. Oxidative dearomatization of o-(hydroxymethyl)phenols followed by π⁴s + π²s cycloaddition furnishes bicyclo[2.2.2]octanes with contiguous keto epoxide groups, which upon ring expansion lead to bicyclo[3.2.2]nonanes endowed with a β,γ-enone chromophore. Unbridging of bicyclo[3.2.2]nonanes upon singlet excitation furnishes embellished cis-hydrindanes.

Key words

oxidative dearomatization - cycloaddition - 1,3-acyl shift - cis-hydrindanes - ring expansion

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