Synthesis of enantiomerically pure oxygen-containing helical heterocycles via stereospecific rearrangement of benzofused-2,2′-diphenoquinone derivatives

[Display omitted] •Synthesis of enantiomerically-pure three types of helicene-like molecules.•Novel rearrangement of helical quinone (benzofused-2,2′-diphenoquinone) derivatives without loss of optical purity.•Chiroptical properties were measured by specific optical rotation and CD spectra.•Selective synthesis of helical molecules depending on the reaction conditions. Three different enantiomerically pure poly-condensed oxygen-containing heterocyclic compounds were synthesized by the rearrangement of enantiomerically pure (P)- and (M)-benzofused-2,2′-diphenoquinones. The three products were: a spiro compound bearing a γ-lactone ring, and two derivatives with a helical structure, one containing a δ-lactone ring and the other oxepin and furan rings. When the helical quinone derivative was heated in solution, the rearrangement proceeded with retention of configuration. Thus, (P)-quinone derivatives gave the corresponding (S)-spiro and (P)-helicene-like derivatives without compromising their enantiomeric purity, and vice versa.