Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds
Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in a one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged in a highly regio-, diastereo-, and enantio-selective Lewis base asymmetric allylic alkylation (AAA) with alkyne-functionalized Morita-Baylis-Hillman (MBH) carbonates. Gratefully, due to the low Lewis base catalyst loading, subsequent gold-catalyzed Friedel-Crafts type cyclization, entailing the formation of fused polycyclic compounds, proceeded efficiently, affording structurally complex, highly enantioenriched products.
Authors
- Rémi Pereira
- Aurélien Blanc (ORCID: https://orcid.org/0000-0003-4240-3281)
- Pierre Locquet
- Emmanuel Riguet (ORCID: https://orcid.org/0000-0002-8926-113X)
- Fabienne Grellepois (ORCID: https://orcid.org/0000-0002-0992-722X)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie (FR)
- Institut de Chimie Moléculaire de Reims (FR)
- Université de Strasbourg (FR)
- Université de Reims Champagne-Ardenne (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-02-21
- DOI
- https://doi.org/10.1021/acs.joc.5c00051
- Citations
- 4
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Agence Nationale de la Recherche
- Université de Strasbourg
- Centre National de la Recherche Scientifique
- Ministère de l'Enseignement supérieur, de la Recherche et de l'Innovation
- Université de Reims Champagne-Ardenne