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Date of Award

Spring 2009

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science



First Advisor

Dr. C. Wade Downey

Second Advisor

Dr. Carol Parish


Abstract: A new aldol-type reaction has been developed that does not require the extremely basic conditions of a traditional aldol reaction nor the previously synthesized enol silane needed for Mukaiyama aldol reactions. Formation of the enol silane occurs in situ, obviating the need for purification of the nucleophile. In the presence of a slight excess of TMSOTf and Hunig’s base, aromatic ketones add to saturated and unsaturated aldehydes and dimethyl acetal electrophiles to yield β-hydroxy and β-methoxy carbonyl compounds, respectively. Current investigation has shown that this method can be extended to the coupling of trimethylsilyl acetate to aldehydes to form β-hydroxy carboxylic acids.