title: Stereoselective α-fluorination of N-acyloxazolidinones at room temperature within 1 h.
abstract: A direct α-fluorination of N-acyloxazolidinones based on the unique reactivity of group IVa metal enolates has been developed. The reaction is an experimentally simple, low-cost, quick, and energy-efficient alternative for asymmetric α-fluorination of N-acyloxazolidinones. Preliminary studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromatic substituents. High diastereoselectivities have been achieved with most substrates tested, and the reaction is typically complete within 1 h at ambient temperature.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara , Santa Barbara, California 93106, United States.
authors.forename: Joseph
authors.initials: J
authors.lastname: Alvarado
authors.forename: Aaron T
authors.initials: AT
authors.lastname: Herrmann
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000475:Alkenes; D000480:Alkynes; D023303:Oxazolidinones