Intramolecular [2 + 2] Photocycloaddition of Benzene Derivatives─Chiral Induction in Cyclodextrin Inclusion Complexes
The cyclodextrin (CD) complexes of several butenyloxybenzonitriles were synthesized and irradiated as aqueous suspensions. An enantioselective intramolecular [2 + 2] or ortho photocycloaddition in such inclusion complexes is described. α-Cyclodextrin and β-cyclodextrin induce chirality in the opposite direction. At the reaction temperature (<7 °C), the enantiomeric excess (ee) is significantly increased (34% for α-CD, -10% for β-CD). The product yield in the cyclodextrin complex (35%) was close to that one of the racemic reaction in solution (42%). A topological analysis describes C<sub>2</sub>-symmetric chiral induction in a C<sub>6</sub>-symmetric host structure (α-Cyclodextrin). In a computational study, the energies of the inclusion complex were calculated for different conformations of compound <b>3a</b>.
Authors
- Agathe Martinez (ORCID: https://orcid.org/0000-0003-1769-2413)
- Arthur Desvals (ORCID: https://orcid.org/0000-0002-6780-0526)
- Norbert Hoffmann (ORCID: https://orcid.org/0000-0002-8615-7476)
- Corentin Lefebvre (ORCID: https://orcid.org/0000-0001-5358-102X)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources (FR)
- Université de Picardie Jules Verne (FR)
- Université de Strasbourg (FR)
- Université de Reims Champagne-Ardenne (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-12-05
- DOI
- https://doi.org/10.1021/acs.joc.5c01616
- Primary Topic
- Photochemistry and Electron Transfer Studies
- Type
- article
- Field-Weighted Citation Impact
- 0.00