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Date of Award
2015
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. C. Wade Downey
Abstract
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.
Recommended Citation
Ingersoll, Jared Andrew, "One-pot enol silane formation-Mukaiyama-Mannich reactions of thioesters in the presence of silyl triflates" (2015). Honors Theses. 913.
https://scholarship.richmond.edu/honors-theses/913