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Title page for ETD etd-07182014-092700

Type of Document Master's Thesis
Author Witt, Jonathan Okrent
URN etd-07182014-092700
Title Umpolung Amide Synthesis Using Free Amino Acids
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Craig W. Lindsley Committee Member
Jeffrey N. Johnston Committee Member
  • amide
  • nitroalkane
  • umpolung amide synthesis
Date of Defense 2014-07-18
Availability unrestricted
Traditional amide synthesis employs a nucleophilic amine, which is reacted with an electrophilic activated carboxylic acid or carboxylic acid surrogate. Recently, colleagues in the Johnston lab introduced an unconventional approach to amide synthesis. In contrast to the standard approach, this new method utilizes an electrophilic amine and nucleophilic carboxylic acid equivalent. This approach, referred to as Umpolung Amide Synthesis (UmAS), was extended to the synthesis of amides from free amino acids. The products of these reactions bear one less protecting group than the analogous products of standard amide forming reactions. In addition, prior work has shown that epimerization does not occur with UmAS reactions. A library of stereochemically pure or enriched dipeptides was synthesized using this approach. In addition, the discovery of a novel reaction that converts α-bromonitroalkanes to carboxylic acids is reported.
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