Synthesis 2022; 54(20): 4622-4628
DOI: 10.1055/a-1882-8128
paper

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

Youssef Nassar
,
Fabienne Fache
,
Béatrice Pelotier
,
Olivier Piva
Y.N. thanks the Ministère de l’Enseignement supérieur, de la Recherche et de l’Innovation (MESRI) for a Ph.D. grant (2019–2021). The Centre National de la Recherche Scientifique (CNRS) and the Université Claude Bernard Lyon 1 are warmly thanked for financial support.


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.

Supporting Information



Publikationsverlauf

Eingereicht: 26. April 2022

Angenommen nach Revision: 23. Juni 2022

Accepted Manuscript online:
23. Juni 2022

Artikel online veröffentlicht:
27. Juli 2022

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