Physical Sciences and Mathematics Commons^™

Aldol Condensations And Nitrile Aldol Reactions Mediated By Trimethylsilyl Trifluoromethanesulfonate, Samuel R. Bottum

Honors Theses

In the presence of excess trimethylsilyl trifluoromethanesulfonate (TMSOTf), ketones and esters undergo aldol addition and dehydration to yield chalcones and cinnamates. This one-pot reaction proceeds through in situ enol silane formation, avoiding the need to pre-form and purify the nucleophile in the Mukaiyama aldol reaction. The stoichiometry of the TMSOTf controls whether the reaction proceeds with simple addition or addition-dehydration. When (trimethylsilyl) acetonitrile is stirred with an aldehyde and TMSOTf, nitrile aldol addition is observed.