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dc.contributor.advisorHarmata, Michael, 1959-en_US
dc.contributor.authorCalkins, Nathan L., 1982-en_US
dc.date.issued2010eng
dc.date.submitted2010 Springen_US
dc.descriptionTitle from PDF of title page (University of Missouri--Columbia, viewed on May 24, 2010).en_US
dc.descriptionThe entire thesis text is included in the research.pdf file; the official abstract appears in the short.pdf file; a non-technical public abstract appears in the public.pdf file.en_US
dc.descriptionDissertation advisor: Dr. Michael Harmata.en_US
dc.descriptionVita.en_US
dc.descriptionIncludes bibliographical references.en_US
dc.descriptionPh. D. University of Missouri--Columbia 2010.en_US
dc.descriptionDissertations, Academic -- University of Missouri--Columbia -- Chemistry.en_US
dc.description.abstractThe synthesis of chiral ligands to tune the reactivity and stereoselectivity of many catalytic asymmetric reactions has been given considerable attention in synthetic organic chemistry over the past decade. This report will show the results of efforts toward the syntheses of several families of enantiomerically pure 2,1-benzothiazine ligands. These ligands are unique in that they contain a chiral sulfoximine. Several 2,1-benzothiazine ligands were prepared in single one-pot syntheses and others in as many as five or more steps for larger heterocycles. An optimized synthetic route will be shown for a very well known Buchwald Hartwig N-arylation of sulfoximines and haloarenes. The synthetic procedure for the N-arylation of sulfoximines synthetic procedure has virtually been unchanged since its introduction in 1998. The new synthesis herein has dramatically improved reaction time and scope for the N-arylation of aryl bromides and aryl chlorides. Until now, aryl chloride based N-arylations gave extremely poor conversions when attempted thermally. Lastly, unsubstituted and 4-phenyl substituted 2,1-benzothiazine lithiation reactivity will be discussed for the sulfoximine stabilized lithium vinyl carbanions. Mono- and di-substitutions are now synthetically possible. New synthetic strategies for accessing the ortho-S-phenyl ring as a viable carbanion will also be shown.en_US
dc.format.extentxv, 273 pagesen_US
dc.identifier.merlinb77789775en_US
dc.identifier.merlinb77789775
dc.identifier.oclc651669134en_US
dc.identifier.otherCalkinsN-042210-D3359en_US
dc.identifier.urihttp://hdl.handle.net/10355/8309
dc.publisherUniversity of Missouri--Columbiaen_US
dc.relation.ispartof2010 Freely available dissertations (MU)en_US
dc.relation.ispartofcommunityUniversity of Missouri-Columbia. Graduate School. Theses and Dissertations. Dissertations. 2010 Dissertations
dc.subject.lcshBenzothiazineen_US
dc.subject.lcshOrganic compounds -- Synthesisen_US
dc.subject.lcshSulfoximinesen_US
dc.title2,1-Benzothiazines: preparation and reactivityen_US
dc.typeThesisen_US
thesis.degree.disciplineChemistry (MU)eng
thesis.degree.grantorUniversity of Missouri--Columbiaeng
thesis.degree.levelDoctoraleng
thesis.degree.namePh. D.eng


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