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dc.contributor.advisor Coltart, Don M en_US
dc.contributor.author Knight, John D. en_US
dc.date.accessioned 2012-09-04T13:15:48Z
dc.date.issued 2012 en_US
dc.identifier.uri http://hdl.handle.net/10161/5829
dc.description Dissertation en_US
dc.description.abstract <p>In the first part of this dissertation, the first asymmetric anti selective aldol addition of a ketone-derived donor that is independent of the structure of the ketone is described. This transformation is facilitated by the use of chiral N-amino cyclic carbamate (ACC) auxiliaries. Under certain conditions, this transformation not only exhibits near perfect anti selectivity and enantioselectivity but also does so via thermodynamic control. Simple manipulation of the reaction conditions allows for the <italic>O</italic>-benzylation of the prepared aldol products and the subsequent removal of the ACC auxiliary to give the &beta;-benzyloxy ketone. Both symmetric and asymmetric ketones can be utilized, and aldol products that would otherwise be difficult if not impossible to prepare via conventional methods are able to be prepared.</p><p>The second part of this dissertation describes the asymmetric total synthesis of (+)- and (-)-mefloquine hydrochloride, a potent antimalarial compound. The synthesis is based on an ACC-mediated asymmetric Darzens reaction between an &alpha;-chloro ketone and a quinoline-based aldehyde. This novel methodology gives a highly enantioenriched epoxide that can be further functionalized to prepare both enantiomers of the antimalarial drug.</p> en_US
dc.subject Organic chemistry en_US
dc.subject ACC en_US
dc.subject anti aldol en_US
dc.subject Darzens reaction en_US
dc.subject mefloquine en_US
dc.title The Anti Selective Aldol Addition of Ketones to Aldehydes Mediated by N-Amino Cyclic Carbamate Chiral Auxiliaries and Its Use in the Asymmetric Total Synthesis of (+)- and (-)-Mefloquine Hydrochloride en_US
dc.type Dissertation en_US
dc.department Chemistry en_US
duke.embargo.months 24 en_US
duke.embargo.release 2014-08-25

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