Diastereoselective Formation of Quaternary Stereocenters in Imidazole N-Oxide Cycloaddition with Fluoroalkenes

Bukowska, Patrycja; Loska, Rafał

Diastereoselective Formation of Quaternary Stereocenters in Imidazole N-Oxide Cycloaddition with Fluoroalkenes

Abstract

Imidazole N-oxides are attractive starting materials for the preparation of complex molecules containing an imidazole ring. Dipolar cycloaddition between 1,1-difluoroalkenes and imidazole N-oxides bearing a chiral auxiliary performed in the presence of oxygen or nitrogen nucleophiles was found to provide access to esters and amides bearing a 2-azaheteroaryl substituent at the α position of the imidazole ring as mixtures of diastereomers that, in most cases, are readily separable. This three-component reaction introduces a new tertiary or quaternary all-carbon stereocenter into the heterocyclic ring at a position originally occupied by hydrogen. Importantly, products containing a trifluoromethyl group attached to this stereocenter are readily available as well.

Keywords

dipolar cycloaddition imidazole N-oxides diastereoselectivity

Citation

Bukowska, P.; Loska, R. Diastereoselective Formation of Quaternary Stereocenters in Imidazole N-Oxide Cycloaddition with Fluoroalkenes. Catalysts 2022, 12, 177. https://doi.org/10.3390/catal12020177

URI

https://depot.ceon.pl/handle/123456789/21497

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Artykuły IChO PAN

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