Intermolecular [3 + 3]-cycloadditions of azides with the Nazarov intermediate.
Tetrasubstituted 1,4-dien-3-ones undergo Nazarov cyclization at low temperature, followed by reaction with organic azides via an apparent [3 + 3]-cycloaddition to give bridged bicyclic triazenes. These products do not appear to be intermediates in the previously described Schmidt-type process to furnish dihydropyridones. The reaction typically occurs with high diastereoselectivity.
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.
Owen
O
Scadeng
Michael J
MJ
Ferguson
F G
FG
West