Iridium-catalyzed enantioselective synthesis of (−)- and (+)-aurantioclavine

A new protocol for generating indoleazepine 9 via an Ir-catalyzed intramolecularly asymmetric amination of secondary allylic alcohol 5 in the presence of Carreira ligand (10) and Sc(OTf)3 is described. This methodology has been exploited in the facile synthesis of natural (−)-aurantioclavine (1), a biosynthetical precursor of communesins, and its unnatural enantiomer (+)-aurantioclavine (ent-1).