KROC-DISSERTATION-2019.pdf (4.44 MB)
New Synthetic Applications of N-Arylnitrones and N-Aryloxyphthalimides
thesis
posted on 2019-08-06, 00:00 authored by Michelle A KrocMy thesis is comprised of two parts. First, the Anderson group has
developed a tunable cascade reaction to access a variety of different N-
heterocycles from α,β-unsaturated N-arylnitrones and electron-deficient
allenes. Due to the constant demand for new N-heterocycles for medicinal
and material applications, we are focused on leveraging this system for the
rapid divergent synthesis of new compounds containing the indole motif.
The cascade reaction is proposed to proceed via common intermediates
that can be directed towards dihydrocarbazoles, dihydropyridoindoles,
bicyclic benzazepinones, and functionalized indoles through the careful
selection of the corresponding hydrogen-bond donor or Lewis acid
catalysts.
The second part of my thesis addresses our method for the dioxygenation of alkenylboronic acids and the synthesis of α-oxygenated ketones using N-hydroxyphthalimide as mild oxidant via a copper-
mediated C–O bond forming reaction and a [3,3]-sigmatropic rearrangement. We extended this reactivity to arylboronic acids for the synthesis of catechols. This approach would allow the regioselectivity of the catechol synthesis to be determined by the constraints of the [3,3]-rearrangement as opposed to the electron-density of the aryl ring.
History
Advisor
Anderson, Laura LChair
Anderson, Laura LDepartment
ChemistryDegree Grantor
University of Illinois at ChicagoDegree Level
- Doctoral
Committee Member
Driver, Tom G Mohr, Justin T Wink, Donald Thatcher, GregSubmitted date
May 2019Issue date
2019-01-24Usage metrics
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