Date of Award
Spring 4-4-2012
Degree Type
Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Hao Xu
Abstract
The ability to generate chiral building blocks is of paramount importance to organic chemists. This problem presents itself most notably at the interface of chemistry and biology, where molecules of only a single enantiomer can induce function to many biological systems. In this context, recent developments in the field of organocatalysis, most notably the employment of chiral N-heterocyclic carbenes (NHCs) have shown much promise.
Our group has recently shown that one possible chiral NHC catalyzed Stetter cyclization product of a conjugated triene, a highly functionalized cyclopentenone, contains both a chiral center and an adjacent conjugated diene. This structure can be easily elaborated to a bicyclic structural motif present in some biologically active natural products from the ginkgolide family, and is difficult to access by other means. The synthesis of novel vinyl stannanes and other coupling substrates involved in the development of the aforementioned reaction discovery are described in this report.
DOI
https://doi.org/10.57709/2767297
Recommended Citation
Toth, Christopher A., "Synthesis of Coupling Substrates for Use in a Highly Enantioselective Conjugated Triene Cyclization Enabled by a Chiral N-Heterocyclic Carbene." Thesis, Georgia State University, 2012.
doi: https://doi.org/10.57709/2767297