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dc.contributor.advisorMartin, Stephen F.en
dc.creatorNeipp, Christopher Ernesten
dc.date.accessioned2011-07-12T21:54:45Zen
dc.date.available2011-07-12T21:54:45Zen
dc.date.issued2003-05en
dc.identifier.urihttp://hdl.handle.net/2152/12293en
dc.descriptiontexten
dc.description.abstractA convergent, stereoselective route to homoallylic sulfonamides has been described. Homoallylic sulfonamides with di- and trisubstituted double bonds were prepared in good yields and with excellent control of alkene geometry via a cuprateinduced 1,2-metalate rearrangement of α-lithiated N-trisyl 2-pyrroline. Removal of the N-trisyl group was achieved by sonication of the sulfonamides in the presence of Li(0) wire and catalytic di-tert-butylbiphenyl. The utility of this method was illustrated by its application toward the synthesis of a squalene synthetase inhibitor. In other efforts, a versatile approach to bridged azabicyclic structures was developed. This process involved the ring-closing metathesis (RCM) of cis-2,6- dialkenyl N-acyl piperidines, which were prepared in six steps from glutarimide or in three steps from 4-methoxypyridine. The N-acyl protecting group of these piperidines played a crucial role in this sequence by stabilization of the C2,C6 bisaxial conformers necessary for their RCM. In this manner, a diverse array of bridged azabicyclic structures were obtained in excellent yields. Application of this RCM strategy toward the synthesis of (±)-cocaine and compounds structurally related to vellosimine has been reported.
dc.format.mediumelectronicen
dc.language.isoengen
dc.rightsCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.en
dc.subjectAminesen
dc.subjectAlkenesen
dc.subjectMetathesis (Chemistry)en
dc.titleI. The synthesis of homoallylic amines via a 1,2-metalate rearrangement; II. The synthesis of bridged azabicyclic structures via ring-closing olefin metathesisen
dc.description.departmentChemistryen
thesis.degree.departmentChemistryen
thesis.degree.disciplineChemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen
dc.rights.restrictionRestricteden


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