Regiochemistry of copper(I)-mediated cyclization reactions of halo-dienamides.
Reaction of 2-substituted dienamides with catalytic amounts of copper halide/tripyridylamine (TPA) furnishes either 5-exo or 6-endo products with the outcome dependent upon the radical initiating unit. Reaction of 3-substituted dienamides produces beta-lactams via a 4-exo cyclization with termination of the reaction occurring via either halogen atom transfer, trapping with oxygen, elimination, or radical-radical coupling depending upon the diene.
Clark
Andrew J
AJ
Department of Chemistry, University of Warwick, Coventry, West Midlands, U.K. msrir@csv.warwick.ac.uk
Geden
Joanna V
JV
Thom
Stephen
S
Wilson
Paul
P
D000577:Amides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization
D000577:Amides; D003300:Copper