Stille Coupling of α-Alkoxybenzylstannanes: Optimization Study and Stereochemical Outcome
dc.contributor.author | Su, Hsin Yao | |
dc.date.accessioned | 2011-08-24 14:00:43 (GMT) | |
dc.date.available | 2011-08-24 14:00:43 (GMT) | |
dc.date.issued | 2011-08-24T14:00:43Z | |
dc.date.submitted | 2011 | |
dc.identifier.uri | http://hdl.handle.net/10012/6117 | |
dc.description.abstract | In order to make the stereospecific palladium-catalyzed cross-coupling of α-alkoxybenzyl-stannanes a useful synthetic methodology, optimization was undertaken to improve the coupling yields between these stannanes and benzoyl chloride as a model electrophilic substrate. Efforts were put into synthesizing and screening of a number of protecting groups for α-hydroxystannane, followed by optimization of reaction parameters for the Stille coupling reaction of different racemic α-alkoxybenzylstannanes. These protecting groups were chosen based on the principle of “complexation-induced proximity effect” to guide the metal catalyst. Upon obtaining an optimized reaction condition, the stereochemical outcome for the cross-coupling of enantiomerically enriched α-(trimethylacetoxy)benzylstannane with benzoyl chloride will be unambiguously presented. Influences by both the palladium ligand and the electronic property of the substituted-benzoyl chloride will be discussed. | en |
dc.language.iso | en | en |
dc.publisher | University of Waterloo | en |
dc.title | Stille Coupling of α-Alkoxybenzylstannanes: Optimization Study and Stereochemical Outcome | en |
dc.type | Master Thesis | en |
dc.pending | false | en |
dc.subject.program | Chemistry | en |
uws-etd.degree.department | Chemistry | en |
uws-etd.degree | Master of Science | en |
uws.typeOfResource | Text | en |
uws.peerReviewStatus | Unreviewed | en |
uws.scholarLevel | Graduate | en |