Correa, Fernando

Publication Search Results

Now showing 1 - 1 of 1

A new tandem strategy for the synthesis of α,β-epoxyketones from terminal alkynes
(2019-05-15) Correa, Fernando; Torres-García, Wildeliz; College of Arts and Sciences - Sciences; Morell, Luis; Guzmán, Aikomarí; Meléndez, Enrique; Department of Chemistry; Pérez, Fernando
Because of its unique reactivity profile and synthetic utility, epoxides have captivated and attracted the organic chemistry community since their discovery. They are valuable precursors of many bioactive natural and unnatural compounds and there is an incessant interest in the development of green methods that give access to these scaffolds efficiently. Herein, we report an unprecedented Darzens reaction that uses an α-mesyloxyketone as substrate for the synthesis of 10 representative examples in moderate to good yield (12-71%). This reaction was then applied in tandem to a known gold-catalyzed alkyne oxidation that made possible the direct conversion of terminal alkynes to α,β-epoxyketones albeit in moderate yields (15-22%). Even though further optimization is needed for the tandem process this method allows for a dramatic and rapid increase in substrate complexity from simple and affordable starting materials.