The Curtius rearrangement is a well-known organic transformation that involves the synthetic preparation and subsequent thermal decomposition of acyl azides into their corresponding isocyanates. Isocyanates can serve as good electrophiles and may be subject to attack by a variety of nucleophilic species to yield amine, carbamate, and urea derivatives. It became of interest to exploit the isocyanate intermediates formed during molecular rearrangement of acyl azides derived from functionalized chiral carboxylic acids. Ultimately, we present a variation on the Curtius reaction in which we are able to synthesize chiral, non-racemic carbamates and ureas that have a potential to be used as asymmetric catalysts. This poster presentation outlines the methodology developed in the refinement of this Curtius rearrangement process.

Synthesis of structurally novel carbamates and ureas derived from the Curtius rearrangement

ACS Spring 2022

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