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dc.contributor.advisorNjardarson, Jon T.en
dc.contributor.authorChogii, Isaac*
dc.creatorChogii, Isaacen
dc.date.accessioned2016-12-09T02:37:00Z
dc.date.available2016-12-09T02:37:00Z
dc.date.issued2016
dc.identifier.urihttp://hdl.handle.net/10150/621558
dc.description.abstractNew Anionic Annulation Reactions and Anion Accelerated Amino-Cope Rearrangement. This dissertation compiles asymmetric anionic reactions of chiral Ellman sulfinyl imines and dienolates to access diverse nitrogen-containing compounds. Chiral sulfinimines and dienolates derived from 𝛾-bromocrotonates reacted diastereoselectively forming 3-pyrrolines and 𝑐𝑖𝑠-vinyl aziridines via a formal [3+2]-annulation and vinylogous 𝑎𝑧𝑎-Darzens reactions respectively. Concise asymmetric syntheses of three natural products have been achieved demonstrating the power of the [3+2]-methodology. Reaction of conjugated sulfinimines with enolates derived from non-halogen containing crotonates, were found to undergo a tandem diastereoselective α,α-addition, and anionic [3,3]-rearrangement affording vinylogous amide products. Synthesis of aromatic imines via 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) initiated oxidative aromatization highlights the synthetic value of the accelerated anion amino-Cope rearrangement.
dc.language.isoen_USen
dc.publisherThe University of Arizona.en
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en
dc.subjectChemistryen
dc.titleNew Anionic Annulation Reactions and Anion Accelerated Amino-Cope Rearrangementen_US
dc.typetexten
dc.typeElectronic Dissertationen
thesis.degree.grantorUniversity of Arizonaen
thesis.degree.leveldoctoralen
dc.contributor.committeememberNjardarson, Jon T.en
dc.contributor.committeememberGlass, Richard S.en
dc.contributor.committeememberMash, Eugene A.en
dc.contributor.committeememberTomat, Elisaen
dc.description.releaseRelease after 01-Jul-2017en
thesis.degree.disciplineGraduate Collegeen
thesis.degree.disciplineChemistryen
thesis.degree.namePh.D.en
refterms.dateFOA2017-07-01T00:00:00Z
html.description.abstractNew Anionic Annulation Reactions and Anion Accelerated Amino-Cope Rearrangement. This dissertation compiles asymmetric anionic reactions of chiral Ellman sulfinyl imines and dienolates to access diverse nitrogen-containing compounds. Chiral sulfinimines and dienolates derived from 𝛾-bromocrotonates reacted diastereoselectively forming 3-pyrrolines and 𝑐𝑖𝑠-vinyl aziridines via a formal [3+2]-annulation and vinylogous 𝑎𝑧𝑎-Darzens reactions respectively. Concise asymmetric syntheses of three natural products have been achieved demonstrating the power of the [3+2]-methodology. Reaction of conjugated sulfinimines with enolates derived from non-halogen containing crotonates, were found to undergo a tandem diastereoselective α,α-addition, and anionic [3,3]-rearrangement affording vinylogous amide products. Synthesis of aromatic imines via 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) initiated oxidative aromatization highlights the synthetic value of the accelerated anion amino-Cope rearrangement.


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