Asymmetric Allylation/Pauson–Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues

Asymmetric allylation of o-iodoarylsulfinylimines
has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent
Sonogashira coupling followed by a diastereoselective intramolecular
Pauson–Khand reaction. In this way, tricyclic amines showing
a unique benzo-fused indenyl backbone were obtained. The methodology
has been applied to the synthesis of amino steroid analogues.