N-triflylphosphoramides have emerged powerful and efficient organocatalysts used in reactions such as 3+2 cycloadditions, Friedel-Crafts alkylation, and intermolecular carbonyl-ene reactions. For a while, our group has been interested in the development of intramolecular ene reactions using organocatalysts. After screening several other Brønsted acids including phosphoric acid derivatives, a strongly acidic N-triflylphosphoramide was found to catalyze the intramolecular carbonyl-ene reaction of citronellal as well as a CF3 ketone derived from citronellic acid. The optimization of the reaction conditions and scope of the reaction will be presented. We also report the 1H NMR studies used to characterize the interaction between the substrate and catalyst.

Intramolecular carbonyl-ene reactions catalyzed by a triflylphosphoramide

251st National Meeting (2016)

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