Secondary Phosphine Oxide Grafted on an Inherently Chiral Calixarene: Synthesis, Resolution, Characterizations, and Catalytic Activity
A secondary phosphine oxide (SPO) unit has been grafted on an inherently chiral calixarene, providing four stereoisomers that were separated by chiral HPLC. These low-symmetry ligands were then used in the palladium-catalyzed isomerization reaction of allylic alcohols. A strong confinement effect was observed: No product or ee was observed with the model SPO cavity-lacking ligand, whereas the calixarene-based SPO provided both catalytic activity and asymmetric induction.
Authors
- Alexandre Martinez (ORCID: https://orcid.org/0000-0002-6745-5734)
- Sara Chentouf (ORCID: https://orcid.org/0000-0003-0695-7260)
- Didier Nuel (ORCID: https://orcid.org/0000-0002-5055-0583)
- Gaëtan Herbette (ORCID: https://orcid.org/0000-0002-3374-2508)
- Jean‐Valère Naubron (ORCID: https://orcid.org/0000-0002-8523-4476)
- Romain Membrat
- Pavel Lhoták (ORCID: https://orcid.org/0000-0003-3617-6596)
- Anne‐Doriane Manick (ORCID: https://orcid.org/0000-0002-8182-9915)
- Lucien Lavaud (ORCID: https://orcid.org/0000-0001-8445-2159)
- Martin Tlustý (ORCID: https://orcid.org/0000-0003-3080-5283)
- Laurent Giordano
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- Aix-Marseille Université (FR)
- Université Paris-Saclay (FR)
- Centrale Méditerranée (FR)
- University of Chemistry and Technology, Prague (CZ)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-12-02
- DOI
- https://doi.org/10.1021/acs.joc.5c02171
- Primary Topic
- Supramolecular Chemistry and Complexes
- Type
- article
- Field-Weighted Citation Impact
- 0.00