Work

Grignard Reagent Addition to Pyridinium Salts: A Catalytic Approach to Chiral 1,4-Dihydropyridines

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Catalytic dearomatization of pyridinium salts is a powerful technique for constructing chiral N -heterocycles, which are crucial in alkaloid natural products and drugs. Despite its potential, progress in metal-catalyzed asymmetric dearomatization of pyridinium derivatives has been limited. Here, we present the enantioselective 1,4-dearomatization of pyridinium salts using Grignard reagents and chiral copper catalysis. This approach yields enantioenriched functionalized 1,4-dihydropyridines. Experimental kinetic isotope effects and density functional theory calculations provide insights into the reaction mechanism, regio- and enantioselectivity, and the rate-limiting step.

Source: ACS Catalysis

DOI: 10.1021/acscatal.4c03520

Authors: Siriphong Somprasong, Marta Castiñeira Reis, Syuzanna R. Harutyunyan

Institutions: University of Groningen, Universidade de Santiago de Compostela, Centro Singular de Investigación en Química Biológica y Materiales Moleculares

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: H2020 European Research Council