Abstract

Aryl alkyl ketones, acetate esters, and acetamides undergo facile one-pot enol silane formation, Mukaiyama aldol addition, and dehydrosilyloxylation in the presence of an amine base and excess trimethylsilyl trifluoromethanesulfonate. The chalcone and cinnamate products are generally recovered in high yield. The relative stoichiometry of the trimethylsilyl trifluoromethanesulfonate and amine base reagents determines whether the reaction yields the β- silyloxy carbonyl product or the α, β -unsaturated carbonyl.

Document Type

Article

Publication Date

2018

Publisher Statement

Copyright © 2018, Tetrahedron Letters.

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