Thermal and Trimethylsilyl Triflate Catalyzed Additions of Allylsilanes to Nitrones

Article abstract of DOI:10.1021/jo00244a021

A new methodology is described for the coupling of allylsilanes and nitrones with trimethylsilyl triflate as a catalyst to afford homoallylhydroxylamines in yields ranging from 70percent to 95percent.Lower yields were obtained with shorter reaction times.The reaction also proceeds intramolecularly, giving mixtures of cis and trans tetrahydropyridines in excellent yield.The TMSOTf-catalyzed process is compared and contrasted with the thermally induced intramolecular nitrone cycloaddition.