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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Ketones undergo in situ enol silane formation in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and an amine base, and subsequently undergo alkylation with propargyl or allyl carboxylates ionized by residual TMSOTf to generate -alkynyl ketones or -unsaturated ketones, respectively. Such reactions proceed due to the ability of TMSOTf to act as both a silylating agent and a Lewis acid. The propargyl or allyl carboxylates react efficiently with aryl-alkyl and alkyl-alky ketones, as well as thioesters. Both aryl and alkyl substitution is tolerated on the propargyl carboxylate at the 3-position, and the 1-position may be substituted by various aryl groups. Similarly, aryl substitution is tolerated at both positions on the allyl carboxylates.
Heafner, Elizabeth D., "Alkylations of ketones with propargyl and allyl carboxylates using TMSOTf" (2019). Honors Theses. 1425.
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