Date of Award


Degree Type


Degree Name

Doctor of Philosophy




Michael Kerr


The previously described intermolecular nitrone - cyclopropane reaction has been adapted into an intramolecular variant. A nitrone, generated in-situ by the addition of a hydroxylamine to an aldehyde, engages in a cycloaddition with a 2-carbon-tethered cyclopropanediester. The products of the reaction are substituted [2.2.2]-aza-oxa- bicyclooctanes that are highly functionalized since a wide degree of flexibility is allowed in the tether linkage. Besides an all sp3-carbon spacer, an unsaturated tether can be used and aromatic and heteroaromatic rings can be incorporated into the tether. Importantly, a mild and high yielding procedure to obtain 1,4-aminoalcohols by reductive N-O bond rupture of these compounds has been developed and was shown to produce substituted cis- l-amino-4-cyclohexanols and cis-1-amino-4-hydroxytetrahydronaphthalenes. An expansion of this methodology was envisioned by the use of a ketonic substrate as a nitrone precursor en route to the synthesis of the erythrinan alkaloid 3- demethoxyerythratidinone and work is underway toward this goal.



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