Cu/Pd dual catalyzed stereoselective construction of vicinal tri- and tetrasubstituted stereocenters connected to chiral α-arylacetonitriles
Herein, we report an optimized Pd/Cu bimetallic catalyst that facilitates the stereoselective allylic alkylation of secondary and tertiary nitriles under mild conditions. This method affords homoallylic nitriles with adjacent tri- and tetrasubstituted stereocenters. Using both racemic and enantioselective catalysts, the system exhibits high regio- and enantioselectivity (ee up to 91%). Mechanistic studies and DFT calculations highlight the key synergistic roles of Pd and Cu in controlling both reactivity and enantioselectivity.
Authors
- Laurine Réset (ORCID: https://orcid.org/0009-0008-3737-8468)
- Hélène Gérard (ORCID: https://orcid.org/0000-0002-8935-9591)
- Caroline West (ORCID: https://orcid.org/0000-0001-7595-6777)
- Pascal Retailleau (ORCID: https://orcid.org/0000-0003-3995-519X)
- Liliane Mimoun
- Isabelle Gillaizeau (ORCID: https://orcid.org/0000-0002-7726-3592)
- Cyril Nicolas (ORCID: https://orcid.org/0000-0002-3748-2205)
- Nicolas Vanthuyne (ORCID: https://orcid.org/0000-0003-2598-7940)
- Florian Heppner (ORCID: https://orcid.org/0009-0003-2930-5019)
- Hamdi Sanaa
Institutions
- Université d'Orléans (FR)
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- Sorbonne Université (FR)
- Laboratoire de Chimie Théorique (FR)
- Centrale Méditerranée (FR)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ra04516a
- Citations
- 1
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.54
Funders
- Agence Nationale de la Recherche
- Sorbonne Université