Selenolactams as Synthetic Intermediates for the Synthesis of Polycyclic Amines via Seleno-Claisen Rearrangements

A highly
diastereoselective α-allylation of selenolactams
with allyl halides is reported. DFT analyses and experimental observations
suggested that this reaction proceeds via a Se-allylation
of the eneselenolates of the lactams followed by a seleno-Claisen
rearrangement. The thus-obtained products could be efficiently transformed
into polycyclic amines using a previously developed sequential addition
of organometallic reagents and ring-closing metathesis.