A Rhodium-Catalyzed [(4+2)+2] Cycloaddition of Allenediene for the Synthesis of Medium-Sized Rings

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dc.contributor.advisorGilbertson, Scott R.
dc.contributor.committeeMemberMay, Jeremy A.
dc.contributor.committeeMemberDo, Loi H.
dc.contributor.committeeMemberDas, Joydip
dc.contributor.committeeMemberHalasyamani, P. Shiv
dc.creatorWang, Dihuang 1991-
dc.date.accessioned2019-05-23T14:32:18Z
dc.date.createdAugust 2018
dc.date.issued2018-08
dc.date.submittedAugust 2018
dc.date.updated2019-05-23T14:32:18Z
dc.description.abstractThe synthesis of the compounds with medium-sized rings, especially those with a 5,8-fused ring system embedded into the structure, had long been pursued due to their ubiquitousness in numerous natural products and pharmaceutical molecules. These rings could be efficiently synthesized using metal-catalyzed higher order cycloaddition. In our studies, a previously-reported Rh-catalyzed [4+2+2] cycloaddition was developed and optimized to generate fused systems with a cyclooctadiene core from allenedienes and external alkynes. Upon screening of various metal complexes, ligands and solvents, a rhodium-BozPHOS complex was found to have the best reactivity. This cycloaddition between allenedienes and alkynes showed moderate yield and good substrate tolerance, showing good synthetic potential.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/10657/3998
dc.language.isoeng
dc.rightsThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).
dc.subjectAllenediene
dc.subjectCycloaddition
dc.subject5,8-fused rings
dc.subjectBozPHOS
dc.subjectRh-catalyzed
dc.titleA Rhodium-Catalyzed [(4+2)+2] Cycloaddition of Allenediene for the Synthesis of Medium-Sized Rings
dc.type.dcmiText
dc.type.genreThesis
local.embargo.lift2020-08-01
local.embargo.terms2020-08-01
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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