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Catalysis inside the Hexameric Resorcinarene Capsule.

Qi Zhang1, Lorenzo Catti1, Konrad Tiefenbacher1,2

  • 1Department of Chemistry , University of Basel , BPR 1096, PO Box 3350, Mattenstrasse 24a , CH- 4002 Basel , Switzerland.

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Supramolecular resorcinarene capsules act as catalysts, offering size and product selectivity similar to enzymes. This research explores their potential in reactions like iminium catalysis and terpene cyclization.

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Molecular capsules mimic enzyme active sites, offering potential advantages in catalysis.
  • Supramolecular host systems are limited due to difficulties in predicting catalytic potential and understanding encapsulation behavior.

Purpose of the Study:

  • Investigate the encapsulation behavior of resorcinarene and pyrogallolarene capsules.
  • Explore the catalytic potential of the resorcinarene capsule (Capsule I) for various organic reactions.

Main Methods:

  • Studied the encapsulation behavior of resorcinarene capsule I and pyrogallolarene capsule II.
  • Applied Capsule I as a catalyst for iminium catalysis, terpene cyclization, and carbonyl-olefin metathesis.

Main Results:

  • Achieved enhanced enantioselectivity in proline-mediated iminium catalysis within Capsule I.
  • Synthesized cyclic monoterpenes eucalyptol and α-terpinene via tail-to-head terpene cyclization inside Capsule I.
  • Demonstrated efficient carbonyl-olefin metathesis using a co-catalytic system of Capsule I and HCl, outperforming solution-phase catalysis.

Conclusions:

  • Supramolecular capsules, despite being in early development, show promise for synthetically relevant catalysis.
  • The confined environment within resorcinarene capsules can lead to unique selectivity and improved catalytic efficiency.