jo9b02921_si_001.cif (367.48 kB)

Synthetic Entry to the 2‑Azatricyclo[4.3.2.04,9]undecane Ring System via Tropone

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posted on 16.01.2020 by Zaki K. Phelan, Philip S. Weiss, Yiqun He, Ziyang Guan, Dasan M. Thamattoor, Daniel R. Griffith
A synthesis of the 2-azatricyclo­[4.3.2.04,9]­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.

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