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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Dr. C. Wade Downey
The addition of aryl thioesters to imines proceeds efficiently in the presence of an amine base and a slight excess of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in one pot. The TMSOTf acts as both a silylating agent and Lewis acid in the case of these reactions. Mannich products are isolated as the free amine without desilylative work up. These one-pot reactions allow for the in situ formation of the requisite enol silane intermediate, and residual TMSOTf acts as a Lewis acid to facilitate Mukaiyama- Mannich addition to imines. By eliminating the necessity to pre-form and purify the enol silane nucleophile, waste generation is reduced and time loss is minimized.
Ingersoll, Jared Andrew, "One-pot enol silane formation-Mukaiyama-Mannich reactions of thioesters in the presence of silyl triflates" (2015). Honors Theses. 913.