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Stereoselective α‑Fluorination of N‑Acyloxazolidinones at Room Temperature within 1 h

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journal contribution
posted on 03.07.2014, 00:00 by Joseph Alvarado, Aaron T. Herrmann, Armen Zakarian
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.