Commodity chemicals in enantioselective iridium-catalyzed carbonyl allylation

dc.contributor.advisorKrische, Michael J.
dc.contributor.committeeMemberHull, Kami L
dc.contributor.committeeMemberSessler, Jonathan L
dc.contributor.committeeMemberWhitman, Christian P
dc.creatorMeyer, Cole Christian
dc.creator.orcid0000-0002-4319-7806
dc.date.accessioned2023-07-28T21:02:42Z
dc.date.available2023-07-28T21:02:42Z
dc.date.created2023-05
dc.date.issued2023-04-13
dc.date.submittedMay 2023
dc.date.updated2023-07-28T21:02:43Z
dc.description.abstractA principal characteristic of a scalable synthetic method is its ability to facilitate the formation of C-C bonds between inexpensive, abundant commodity chemicals without producing stoichiometric metallic byproducts. To this end, a suite of enantioselective iridium-catalyzed reactions for the direct transformation of commodity chemicals to value-added products is described. The reductive couplings discussed herein utilize alcohols as terminal reductants, and therefore do not produce stoichiometric metallic byproducts. The work presented in this dissertation includes 1) a review on couplings of methanol, ethanol, and formaldehyde with π-unsaturated pronucleophiles, and primary research articles describing enantioselective iridium-catalyzed carbonyl allylations involving commodity chemicals 2) allene gas, a petrochemical feedstock, 3) ethanol, a biorenewable C2 feedstock, 4) oxetan-3-one and azetidin-3-ones, abundant building blocks deployed in medicinal chemistry, 5) allyl alcohol, a reliably-sourced acrolein proelectrophile, and its application to the total synthesis of three amphidinolide natural products, and 6) acetyl 1,3-propanediol, a derivative of 1,3-propanediol, as an improved acrolein proelectrophile.
dc.description.departmentChemistry
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/2152/120705
dc.identifier.urihttp://dx.doi.org/10.26153/tsw/47540
dc.language.isoen
dc.subjectIridium
dc.subjectCatalysis
dc.subjectCommodity chemicals
dc.subjectAsymmetric
dc.subjectEnantioselective
dc.subjectCarbonyl addition
dc.titleCommodity chemicals in enantioselective iridium-catalyzed carbonyl allylation
dc.typeThesis
dc.type.materialtext
thesis.degree.departmentChemistry
thesis.degree.disciplineChemistry
thesis.degree.grantorThe University of Texas at Austin
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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