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

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 s...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-07, Vol.79 (13), p.6206-6220
Main Authors: Alvarado, Joseph, Herrmann, Aaron T, Zakarian, Armen
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Alkynes - chemistry
Catalysis
Halogenation
Molecular Structure
Oxazolidinones - chemistry
Stereoisomerism
Temperature
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500957d