Date of Award
2026
Document Type
Thesis
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. C. Wade Downey
Abstract
Aldehydes and olefins react in the presence of base and TMSOTf to yield homoallylic alcohols. In this net ene reaction, TMSOTf acts as a Lewis acid to activate the aldehyde, leading to a strong oxygen-silicon bond that acts as a driving force in the reaction. In the proposed mechanism, the α-methylstyrene attacks the carbonyl carbon of the TMSOTf-activated aldehyde to produce a carbocationic intermediate. Elimination using a relatively bulky base (2,6-lutidine) provides the homoallylic alcohol. This reaction has proven robust in terms of the aldehyde and olefin scope.
Recommended Citation
Mock, Alexandra, "Net carbonyl ene reactions of olefins with aldehydes" (2026). Honors Theses. 1918.
https://scholarship.richmond.edu/honors-theses/1918