10.1021/acs.joc.9b02921.s001 Zaki K. Phelan Zaki K. Phelan Philip S. Weiss Philip S. Weiss Yiqun He Yiqun He Ziyang Guan Ziyang Guan Dasan M. Thamattoor Dasan M. Thamattoor Daniel R. Griffith Daniel R. Griffith Synthetic Entry to the 2‑Azatricyclo[4.3.2.0<sup>4,9</sup>]undecane Ring System via Tropone American Chemical Society 2020 allylamine Synthetic Entry azatricyclo diene intramolecular amine tricarbonyl Tropone azatricyclic bridged 2- parameter synthesis Diel dienophile tether length aza-Michael Boc-protection dienophile substitution patterns oxidative undecane Ring System demetallation variety Azatricyclo 2020-01-16 18:04:19 Dataset https://acs.figshare.com/articles/dataset/Synthetic_Entry_to_the_2_Azatricyclo_4_3_2_0_sup_4_9_sup_undecane_Ring_System_via_Tropone/11629338 A synthesis of the 2-azatricyclo­[4.3.2.0<sup>4,9</sup>]­undecane ring systema hitherto unreported bridged azatricyclic ring systembeginning from tricarbonyl­(tropone)iron and allylamine was accomplished in three steps: (1) aza-Michael addition of allylamine to tricarbonyl­(tropone)­iron; (2) Boc-protection of the resulting secondary amine; and (3) oxidative demetallation leading to a spontaneous intramolecular Diels–Alder reaction. The effect of a variety of parameters on the intramolecular Diels–Alder reaction was investigated, including diene and dienophile substitution patterns and dienophile tether length.