AI Article Synopsis
- - A new type of bridged azatricyclic ring system, 2-azatricyclo[4.3.2.0]undecane, was successfully synthesized using tricarbonyl(tropone)iron and allylamine through a three-step chemical process.
- - The synthesis steps included an aza-Michael addition, followed by Boc-protection of the resulting secondary amine, and concluded with oxidative demetallation that triggered an intramolecular Diels-Alder reaction.
- - The research also explored how different factors, such as the substitution patterns of the diene and dienophile, as well as the length of the dienophile tether, influenced the outcome of the Diels-Alder reaction.
Article Abstract
A synthesis of the 2-azatricyclo[4.3.2.0]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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| http://dx.doi.org/10.1021/acs.joc.9b02921 | DOI Listing |
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