A Tandem Amino-Cope Rearrangement/Enamine Alkylation Reaction

Article abstract of DOI:10.1055/s-1997-3248

Thermally induced [3,3]-sigmatropic rearrangement of 3-amino-1,5-diene substrates occurs to give the corresponding enamine products in high yield and with excellent trans:cis enamine selectivity. The enamine produced during the amino-Cope rearrangement has been directly derivatized, representing the first report of a tandem amino-Cope rearrangemenl/enamine alkylation reaction. The potential of this novel synthetic strategy is outlined.