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Date of Award

Spring 2011

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science



First Advisor

Dr. C. Wade Downey


Ynoate esters carry the ability to undergo two sequential 1,4-additions in a single reaction flask, provided that the nascent enoate or allenolate anion can be protonated in situ. By employing a catalytic amount of trialkylamine base, significant progress has been made toward this goal for thiol nucleophiles and cyclopentadiene. Amine-catalyzed thioconjugate addition affords ?-thio enoates with high geometric purity, which are oxidized in situ in the presence of LiClO4 to the corresponding Z-?-sulfones that further react with cyclopentadiene, resulting in Diels–Alder products that are bicyclic, stereochemically complex carboxylic acid derivatives.