A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates.

Armen Zakarian, Aaron T Herrmann, Lindsay L Smith

Journal: Journal of the American Chemical Society 2012;134(16):6976-9

PMID: 22486383

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Abstract

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

Address: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.

DOI: 10.1021/ja302552e

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https://doi.org/10.1021/ja302552e

MeSH Terms: Catalysis, Free Radicals, Ketones, Methylation, Molecular Conformation, Organometallic Compounds, Oxazolidinones, Ruthenium, Stereoisomerism, Zirconium