Enantioselective -heterocyclic Carbene-catalyzed Nucleophilic Dearomatization of Alkyl Pyridiniums

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2017 Oct 10

PMID 28989683

Citations 15

Authors

Darrin M Flanigan

Tomislav Rovis

Affiliations

Soon will be listed here.

Abstract

NHC-catalyzed nucleophilic dearomatization of alkyl pyridiniums has been achieved to generate 1,4-dihydropyridines with high enantioselectivity. This is a rare example of catalytic, asymmetric addition of a nucleophile to the activated pyridinium that prefers C-4 functionalization leading to the 1,4-dihydropyridine with high selectivity.

Citing Articles

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

Somprasong S, Castineira Reis M, Harutyunyan S ACS Catal. 2024; 14(17):13030-13039.

PMID: 39263543 PMC: 11385375. DOI: 10.1021/acscatal.4c03520.

NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates.

Wu T, Tatton M, Greaney M Angew Chem Weinheim Bergstr Ger. 2024; 134(15):e202117524.

PMID: 38504766 PMC: 10947523. DOI: 10.1002/ange.202117524.

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.

Escolano M, Gavina D, Alzuet-Pina G, Diaz-Oltra S, Sanchez-Rosello M, Del Pozo C Chem Rev. 2024; 124(3):1122-1246.

PMID: 38166390 PMC: 10902862. DOI: 10.1021/acs.chemrev.3c00625.

Construction of 1,4-Dihydropyridines: The Evolution of C4 Source.

Song S, Wang Y, Yu F Top Curr Chem (Cham). 2023; 381(5):30.

PMID: 37749452 DOI: 10.1007/s41061-023-00440-x.

Recent Progresses in the Catalytic Stereoselective Dearomatization of Pyridines.

Comparini L, Pineschi M Molecules. 2023; 28(17).

PMID: 37687015 PMC: 10488975. DOI: 10.3390/molecules28176186.

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