A copper (II)-catalyzed, sequential Michael–aldol reaction for the preparation of 1, 2-dihydroquinolines

AM Wagner, CE Knezevic, JL Wall, VL Sun, JA Buss…

Index: Wagner, Anna M.; Knezevic, Claire E.; Wall, Jessica L.; Sun, Victoria L.; Buss, Joshua A.; Allen, Leeann T.; Wenzel, Anna G. Tetrahedron Letters, 2012 , vol. 53, # 7 p. 833 - 836

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Citation Number: 13

Abstract

A copper (II)-catalyzed, sequential Michael addition-aldol condensation reaction of N- carboxybenzyl-protected aminobenzaldehyde with various α, β-unsaturated N-acyl pyrroles is described. Substrate scope was found to include both aryl and aliphatic N-acyl pyrroles as the Michael acceptors, and isolated product yields as high as 93% were observed. The use of acetonitrile as the reaction solvent proved to be crucial for catalysis, both to function as ...