Highly efficient amine organocatalysts based on bispidine for the asymmetric Michael addition of ketones to nitroolefins

A highly diastereoselective and enantioselective Michael addition of cyclohexanone, acetone and other ketones to nitroolefins was developed by the use of an amine organocatalyst based on bispidine. Additionally, a theoretical study of transition structures revealed that this bispidine-based primary-secondary amine catalyst could serve through an enamine intermediate and H-bond interaction, which was important for the reactivity and selectivity of this reaction.