Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

Abstract

Starting from readily available cyclic homoallylic alcohols, a Prins reaction allowed the formation of a bicyclic tetrahydropyranyl carbocation intermediate that is only trapped by electron-rich aromatic rings according a further intramolecular Friedel–Crafts reaction leading to new [4.4.3]propellane structures.

Key words

Prins reaction - tetrahydropyrans - Friedel–Crafts reaction - tandem - propellanes

Publication History

Received: 26 April 2022

Accepted after revision: 23 June 2022

Accepted Manuscript online:
23 June 2022

Article published online:
27 July 2022

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