Enantioselective Rauhut-Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

beta-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut-Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Automated summary

This study demonstrates the enantioselective conversion of beta-substituted acrylamides to enantioenriched quinolones using electron-withdrawing protection and moderate nucleophilicity N-heterocyclic carbenes. The reaction shows complete diastereoselectivity, good yield, and modest enantioselectivity. Computational studies support the concept of decreased amide bond character with electron-withdrawing protection of the nitrogen.