Département de chimie moléculaire

α-Diazo β-hydroxyamino esters, readily obtained by the addn. of lithiated Et diazoacetate to cyclic nitrones, react smoothly in the presence of metal catalysts to produce ketonitrones. This transformation results from a selective 1,2-hydride shift of the metal carbenoid intermediates. The process is particularly efficient for diazo-N-hydroxypyrrolidine systems. For diazo-N-hydroxypiperidine substrates, C-H insertion can be a competitive reaction. [on SciFinder(R)]