Fused piperidinones were assembled from chiral allylsilanes possessing
an oxime moiety using a stereocontrolled formal [2+2+2] radical-ionic
process. The cascade involves the addition of an α-iodo
ester to an ene oxime, which is then followed by a 5-exo-trig cyclization onto the aldoxime
function producing an alkoxyaminyl radical species that finally
lactamizes to afford piperidinones. Application of the radical cascade
to ketoximes led instead to cyclopentanes incorporating two ester
fragments as a result of a recombination process.
radical reactions - silicon - domino reactions - piperidines - cyclizations