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 systema hitherto unreported bridged azatricyclic ring
systembeginning 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.