A DFT study of the asymmetric (S)-5-(pyrrolidin-2-yl)-1H-tetrazole catalyzed Michael addition of carbonyl compounds to nitroalkenes

The role of the (S)-5-(pyrrolidin-2-yl)-1H-tetrazole in the asymmetric organocatalyzed Michael addition of carbonyl compounds to nitroalkenes has been studied using DFT methods at the B3LYP/6-31G∗∗ computational level. For the C–C bond-formation step, several reactive channels have been analyzed. The B3LYP/6-31G∗∗ results, which are in reasonable agreement with the experiments, allow us to explain the stereoselectivity and the increase of the reactivity achieved by an intramolecular HB between the acid hydrogen of the tetrazole moiety and one oxygen atom of the nitroalkene.

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