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dc.contributor.advisorHarmata, Michael, 1959-eng
dc.contributor.authorCalkins, Nathan L., 1982-eng
dc.date.issued2010eng
dc.date.submitted2010 Springeng
dc.descriptionTitle from PDF of title page (University of Missouri--Columbia, viewed on May 24, 2010).eng
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.eng
dc.descriptionDissertation advisor: Dr. Michael Harmata.eng
dc.descriptionVita.eng
dc.descriptionIncludes bibliographical references.eng
dc.descriptionPh. D. University of Missouri--Columbia 2010.eng
dc.descriptionDissertations, Academic -- University of Missouri--Columbia -- Chemistry.eng
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.eng
dc.format.extentxv, 273 pageseng
dc.identifier.merlinb77789775eng
dc.identifier.merlinb77789775eng
dc.identifier.oclc651669134eng
dc.identifier.otherCalkinsN-042210-D3359eng
dc.identifier.urihttp://hdl.handle.net/10355/8309eng
dc.publisherUniversity of Missouri--Columbiaeng
dc.relation.ispartof2010 Freely available dissertations (MU)eng
dc.relation.ispartofcommunityUniversity of Missouri-Columbia. Graduate School. Theses and Dissertations. Dissertations. 2010 Dissertationseng
dc.subject.lcshBenzothiazineeng
dc.subject.lcshOrganic compounds -- Synthesiseng
dc.subject.lcshSulfoximineseng
dc.title2,1-Benzothiazines: preparation and reactivityeng
dc.typeThesiseng
thesis.degree.disciplineChemistry (MU)eng
thesis.degree.grantorUniversity of Missouri--Columbiaeng
thesis.degree.levelDoctoraleng
thesis.degree.namePh. D.eng


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