Regioselective Addition of Organolithium Reagents to Fluorinated Proline Amides: Insights from Experiment and Theory
Abstract Herein, we present a regioselective addition–elimination reaction involving organolithium reagents and fluorinated proline‐derived amides as Michael acceptors. This transformation offers a rare example of exclusive 1,2‐addition over 1,4‐addition in a system bearing electron‐withdrawing fluoroalkenes. Combined experimental and DFT studies confirm a strong preference for the 1,2‐addition. The complete regioselectivity observed in this system provides a valuable model for predicting the outcome of similar reactions with fluorinated substrates.
Authors
- Monika Bilska‐Markowska (ORCID: https://orcid.org/0000-0002-9024-5479)
- Marcin Kaźmierczak (ORCID: https://orcid.org/0000-0003-0199-9197)
- Tomasz Siodła (ORCID: https://orcid.org/0000-0003-3429-5321)
Institutions
- Adam Mickiewicz University in Poznań (PL)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2025-10-31
- DOI
- https://doi.org/10.1002/slct.202505278
- Primary Topic
- Advanced Synthetic Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Infrastruktura PL-Grid
- Wroclawskie Centrum Sieciowo-Superkomputerowe, Politechnika Wroclawska
- Academic Computer Centre Cyfronet, AGH University of Science and Technology