Short Domino Sequence to Dioxa[4.3.3]propellanes

Abstract

A variety of dioxa[4.3.3]propellanes are efficiently obtained starting from a dehydrotetramer of 2,4-dimethylphenol. The final installation of the phenol component requires a domino sequence based on electrophilic substitution and a ketalization process. The molecular structure of these dioxa[4.3.3]propellanes was elucidated by 2D NMR techniques as well as X-ray analysis of suitable single crystals. Most of these polycyclic products were formed with high regio- and diastereoselectivity.

propellanes - phenols - polycycles - domino reaction - regioselectivity

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Seebach’s reagent: a mixture of phosphomolybdic acid (25 g), cerium(IV) sulfate (7.5 g), H₂O (500 mL), and concd H₂SO₄ (25 mL).