Work

Stereoselective Fe-Catalyzed Decoupled Cross-Couplings: Chiral Vinyl Oxazolidinones as Effective Radical Lynchpins for Diastereoselective C(sp2)–C(sp3) Bond Formation

Year: 2024

Type: article

Abstract: Modular, catalytic, and stereoselective methods for the dicarbofunctionalization of alkenes can streamline the synthesis of chiral active pharmaceutical ingredients (APIs) and agrochemicals. However, despite the inherent attractive properties of iron as catalysts for practical pharmaceutical synthesis (i.e., less expensive, more abundant, less toxic, and lower carbon footprint in comparison to other transition metals), iron-based catalytic methods that enable highly stereoselective dicarbofunctionalization of alkenes are lacking. Herein, we report the use of readily available chiral vinyl oxazolidinones as effective chiral radical lynchpins to enable practical and diastereoselective (up to 1:78 dr) Fe-catalyzed dicarbofunctionalization with fluoroalkyl halides and hetero(aryl) Grignard reagents. Experimental and computational mechanistic studies are carried out to elucidate the origin of stereoinduction and to build a stereochemical model for the rational reaction design.

Source: ACS Catalysis

DOI: 10.1021/acscatal.4c04568

Authors: Tapas Maity, Ángel Rentería-Gómez, Osvaldo Gutierrez

Institution: Texas A&M University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Institutes of Health, National Institute of General Medical Sciences