Aldol Condensations and Nitrile Aldol Reactions Mediated by Trimethylsilyl Trifluoromethanesulfonate
Date of Award
2020
Document Type
Thesis
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. C. Wade Downey
Abstract
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.
Recommended Citation
Bottum, Samuel R., "Aldol Condensations and Nitrile Aldol Reactions Mediated by Trimethylsilyl Trifluoromethanesulfonate" (2020). Honors Theses. 1468.
https://scholarship.richmond.edu/honors-theses/1468