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Synthesis 2022; 54(24): 5471-5478
DOI: 10.1055/a-1911-6793
DOI: 10.1055/a-1911-6793
paper
Organocatalytic Synthesis of Benzimidazole Derivatives
This study was supported by grants from Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT) (PICT 2016 0861) and Universidad Nacional de Quilmes (UNQ).
Abstract
A synthetic route for the production of chiral derivatives of benzimidazole is presented. Different commercially available amines are evaluated as organocatalysts for the stereoselective aldol addition of N1-benzimidazolyl acetaldehyde, previously prepared by N-alkylation of benzimidazole, with cyclic ketones. When cyclohexanone was used, l-prolinamide proved to be the most efficient catalyst, giving (S)-2-((R)-2-(1H-benzo[d]imidazol-1-yl)-1-hydroxyethyl)cyclohexanone in 92% yield, 90% ee and 92:8 dr (anti/syn).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1911-6793.
- Supporting Information
Publication History
Received: 31 May 2022
Accepted after revision: 28 July 2022
Accepted Manuscript online:
28 July 2022
Article published online:
15 September 2022
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For reviews on structure–activity relationship studies of benzimidazole-based molecules, see:
For N-alkylation strategies, see: