Carboxylate carbenes have the potential to become versatile building blocks for organic synthesis, as their nucleophilic reactivity is unique among related carbonyl carbenes that initially express electrophilic character.  Although the synthesis of carboxylate carbenes has been previously realized, it was primarily achieved for the purpose of a physical investigation, precluding the need for an optimized synthetic route.  For this body of research, a new strategy is being developed to synthesize a-diazocarboxylic acids, the direct precursors of carboxylate carbenes.  The synthesis can be approached from two different classes of starting material and involves the exploration and optimization of carboxylic acid protection and deprotection, as well as carbonyl a-diazotization.

Developing a new synthesis of a-diazocarboxylic acids

247th National Meeting (2014)

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