Work

Regioselective Addition of Organolithium Reagents to Fluorinated Proline Amides: Insights from Experiment and Theory

Year: 2025

Type: article

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.

Source: ChemistrySelect

DOI: 10.1002/slct.202505278

Authors: Marcin Kaźmierczak, Tomasz Siodła, Monika Bilska‐Markowska

Institution: Adam Mickiewicz University in Poznań

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Infrastruktura PL-Grid, Wroclawskie Centrum Sieciowo-Superkomputerowe, Politechnika Wroclawska, Academic Computer Centre Cyfronet, AGH University of Science and Technology

OpenAlex ID: W4415759317

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Cites: 33

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