Resorcin[4]arene Hexameric Capsule as a Supramolecular Catalyst in Elimination and Isomerization Reactions

  1. Tommaso LorenzettoORCID Logo,
  2. Fabrizio FabrisORCID Logo and
  3. Alessandro ScarsoORCID Logo

Submitting author affiliation: Università Ca' Foscari di Venezia, Mestre Venezia, Italy

Beilstein Arch. 2022, 20226. https://doi.org/10.3762/bxiv.2022.6.v1

Published 07 Feb 2022

  • Preprint

Abstract

The hexameric resorcin[4]arene capsule as a self-assembled organocatalyst promotes a series of reactions like the water elimination from 1,1-diphenylethanol, the isomerization of α-pinene and β-pinene preferentially to limonene and minor amounts of camphene, and the carbonyl-ene Prins cyclization of (S)-citronellal preferentially to isopulegol. The role of the supramolecular catalyst consists in promoting the protonation of the substrates leading to the formation of cationic intermediates that are stabilized within the cavity with consequent peculiar features in terms of acceleration and product selectivity. In all cases the catalytic activity displayed by the hexameric capsule is remarkable if compared to many other strong Brønsted or Lewis acids

Keywords: encapsulation, cationic intermediates, supramolecular catalysis, resorcin[4]arene hexamer, organocatalysis

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Lorenzetto, T.; Fabris, F.; Scarso, A. Beilstein Arch. 2022, 20226. doi:10.3762/bxiv.2022.6.v1

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