A longstanding challenge in asymmetric catalysis is the activation of carboxylic acids, especially as nucleophiles in addition reactions. Carboxylic acids are ubiquitous in nature, rendering them attractive substrates. Our initial investigations of bis(amidine)-based chiral proton complexes in iodolactonizations established that bifunctional activation of an iodonium source and the carboxylic acid could lead to high enantioselection. This work evaluated a carboxylic acid substrate constrained to monofunctional activation, owing to the bridged bicyclic transition state required for cyclization. We report preliminary findings for the enantioselective iodolactonization of 1,4-cyclohexadienes using bis(amidine)-based catalysts.

Carboxylic acid activation: Investigation of an enantioselective iodolactonization of 1,4-cyclohexadienes

255th National Meeting (2018)

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