Synthesis of stereodefined, acetoacetate-derived enol triflates and their synthetic utility

Date
2013
Authors
Babinski, David J.
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Abstract

The following dissertation will provide a simple, general protocol for the stereoselective synthesis of acyclic, acetoacetate-derived enol triflates. Despite the importance of enol triflates as synthons in synthetic organic chemistry, the inability to control the stereochemistry about the double bond has prevented their full utility from being realized. This dissertation will address an unmet need in organic chemistry by presenting a simple procedure to access both enol triflate isomers selectively. Moreover, this dissertation will demonstrate the synthetic utility of enol triflate by disclosing a methodology for their conversion to pyrazoles, a class of molecules found in a wide array of biologically active molecules. Lastly, this dissertation will elaborate how enol triflates provide a simple avenue for the study of the aromatic Cope rearrangement.

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Keywords
Aromatic Cope, Enol Triflate, Pyrazole
Citation
Department
Chemistry