Date of Award
Bachelor of Science
Biochemistry & Molecular Biol.
Dr. C. Wade Downey
- A one-pot three-step Diels–Alder reaction sequence of ethyl propiolate and thiols can be performed to produce high yields of complex bicyclic products. A KOt-Bu-catalyzed thioconjugate addition of thiols to enoates, oxidation of the generated thioenoate by mCPBA, and Li-catalyzed Diels–Alder addition of cyclopentadiene occur in situ, without any purification of intermediates.
- Stereoselectivity of the Diels–Alder product was examined by utilizing a chiral sulfone substrate. It was determined that these substrates were unable to provide significant stereochemical control.
- Silylation of 3-phenylpropionitrile is achieved at the α-position with trimethylsilyl trifluoromethanesulfonate and trialkylamine base. Catalyzed by tetrabutylammonium acetate (2.5 mol%), the silylated nitrile reacts in a crossed aldol reaction with a variety of aldehydes to produce β-hydroxynitriles after desilylation.
Mueller, Carly, "One-pot Heteroconjugate addition-diels-alder reactions and acetate-catalyzed aldol reactions of α-silyl nitriles" (2014). Honors Theses. 874.