Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes

Three-component reactions of nitroalkanes, acrylamides, and aldehydes by using a catalytic amount of KOH in DMSO gave beta '-hydroxy-gamma-nitro amides. Mechanistic studies suggested that the reactions proceeded by domino Michael/aldol reactions. The highly nucleophilic nature of transient amide enolates that were formed by Michael addition of nitronate anions to acrylamides in DMSO enabled the realization of catalytic intermolecular aldol reactions of amide enolates in the presence of acidic nitroalkanes.

Automated summary

The three-component reactions of nitroalkanes, acrylamides, and aldehydes using catalytic amount of KOH in DMSO resulted in the formation of beta '-hydroxy-gamma-nitro amides. Mechanistic studies showed that the reactions proceeded through domino Michael/aldol reactions.