Date of Award

Spring 2016

Project Type


Program or Major


Degree Name

Master of Science

First Advisor

Charles K Zercher

Second Advisor

Arthur H Greenberg

Third Advisor

Christopher F Bauer


The investigation of homologation-cyclopropanation in β-diketones revealed the involvement of two donor-acceptor cyclopropane intermediates. Cyclopropanoxide rearrangements were accomplished using reaction conditions other than zinc-carbenoid. Ring fragmentation within chain-extended tertiary cyclopropanoxides was investigated under acidic and basic reaction conditions.

Tandem chain extension-aldol reaction and lactonization were accomplished using α-carboxyester imides. A diastereomeric mixture of substituted γ-lactones (cis and trans) was isolated and characterized by NMR studies. Increased diastereomeric ratios of the trans substituted γ-lactones versus their cis counterparts were attributed towards increased syn-aldol selectivity due to chelation of the zinc-bound ester enolate with the imide carbonyl of the chiral auxiliary.