Date of Award
4-22-2022
Document Type
Thesis
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Wade Downey
Abstract
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, acylated thiones undergo Aldol and Mannich reactions with aldehydes and nitrones to yield complex nitrogen-containing compounds. The use of a chiral metal-ligand complex is hypothesized to accelerate the reaction and increase stereochemical control during product formation. N-Alkylindoles undergo Friedel-Crafts alkylation with acetates in the presence of TMSOTf and 2,6-lutidine to produce 3-alkyl indoles. Varying Substitution on the indole at the 5 position and removal of the alkyl group from the 1 position both show continued reactivity at the 3 position even in the presence of TMSOTf.
Recommended Citation
Bicalho, Bianco, "Towards Asymmetric Mannich Reactions and Alkylation of Indoles" (2022). Honors Theses. 1633.
https://scholarship.richmond.edu/honors-theses/1633