Reversing the stereoselectivity of intramolecular [2+2] photocycloaddition utilizing cucurbit[8]uril as a molecular flask

Xujun Qiu; Jasmin Seibert; Olaf Fuhr; Frank Biedermann; Stefan Bräse

doi:10.1039/d3cc05783f

Reversing the stereoselectivity of intramolecular [2+2] photocycloaddition utilizing cucurbit[8]uril as a molecular flask

Chem Commun (Camb). 2024 Mar 19;60(24):3267-3270. doi: 10.1039/d3cc05783f.

Authors

Xujun Qiu¹, Jasmin Seibert¹, Olaf Fuhr^{2

3}, Frank Biedermann², Stefan Bräse^{1

4}

Affiliations

¹ Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany. braese@kit.edu.
² Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany. frank.biedermann@kit.edu.
³ Karlsruhe Nano Micro Facility (KNMFi), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.
⁴ Institute of Biological and Chemical Systems-Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.

PMID: 38465702
DOI: 10.1039/d3cc05783f

Abstract

Macrocyclic hosts, such as cucurbit[8]uril (CB8), can significantly influence the outcomes of chemical reactions involving encapsulated reactive guests. In this study, we demonstrate that CB8 completely reverses the stereoselectivity of intramolecular [2+2] photo-cycloaddition reactions. Notably, it was also found that CB8 can trigger the unreactive diene to be reactive.