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dc.contributor.authorDeGuzman, Joseph Christopheren_US
dc.date.accessioned2014-03-14T20:13:23Z
dc.date.available2014-03-14T20:13:23Z
dc.date.issued2006-05-31en_US
dc.identifier.otheretd-06192006-161356en_US
dc.identifier.urihttp://hdl.handle.net/10919/28079
dc.description.abstractMemory of chirality (MOC) is an emerging strategy in asymmetric synthesis. It has been applied to enolate chemistry, reactions involving carbocation intermediates, and to radical systems. In this strategy the chirality of an enantiopure reactant is transferred to the dynamic chirality of a reactive intermediate to produce stereospecific product. 1,4-Benzodiazepin-2-ones have been described as a â privilegedâ structure in medicinal chemistry. In addition to their uses as anxiolytics (Valium ®) and anti-epileptic agents (Clonopin ®), they have shown activity as HIV Tat antagonist, ras farnesyltransferase inhibitors in cancer cells, and antiarrhythmic agents. Because of the utility of this scaffold in the area of medicinal chemistry, it has served as a template in libraries for tens of thousands of compounds. Despite the vast diversity of 1,4-benzodiazepin-2-ones, there are few routes to enantiomerically enriched 3,3-disubstituted benzodiazepines containing a â quaternaryâ stereogenic center. This research will discuss the stereochemical properties of 1,4-benzodiazepin-2-ones, and provide a novel approach to synthesize enantiomerically enriched â quaternaryâ benzodiazepines with stereogenic centers through MOC, without the use of external chiral sources.en_US
dc.publisherVirginia Techen_US
dc.relation.haspartDissertation.pdfen_US
dc.rightsI hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to Virginia Tech or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report.en_US
dc.subjectenolateen_US
dc.subjectaxial chiralityen_US
dc.subjectquaternaryen_US
dc.subjectracemizationen_US
dc.subjectbenzodiazepineen_US
dc.subjectconformeren_US
dc.subjectMemory of chiralityen_US
dc.subjectenantiomeric excessen_US
dc.subjectdynamic chiralityen_US
dc.titleMemory of Chirality in 1,4-Benzodiazepin-2-onesen_US
dc.typeDissertationen_US
dc.contributor.departmentChemistryen_US
dc.description.degreePh. D.en_US
thesis.degree.namePh. D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen_US
thesis.degree.disciplineChemistryen_US
dc.contributor.committeechairCarlier, Paul R.en_US
dc.contributor.committeememberTanko, James M.en_US
dc.contributor.committeememberKingston, David G. I.en_US
dc.contributor.committeememberHanson, Brian E.en_US
dc.contributor.committeememberEtzkorn, Felicia A.en_US
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-06192006-161356/en_US
dc.date.sdate2006-06-19en_US
dc.date.rdate2006-08-11
dc.date.adate2006-08-11en_US


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