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dc.contributor.advisorWard, Dale E.en_US
dc.creatorGillis, Harold Martinen_US
dc.date.accessioned2007-09-24T12:25:38Zen_US
dc.date.accessioned2013-01-04T04:59:46Z
dc.date.available2008-09-24T08:00:00Zen_US
dc.date.available2013-01-04T04:59:46Z
dc.date.created2007en_US
dc.date.issued2007en_US
dc.date.submitted2007en_US
dc.identifier.urihttp://hdl.handle.net/10388/etd-09242007-122538en_US
dc.description.abstractMeso 1,9-diketones (six to seven stereocenters)are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution to give the mono-TMS enol ethers in >90% yields based on recovered starting material (BORSM) and >90% ee. The developed methodology was applied in synthetic studies towards the asymmetric synthesis of denticulatin A.en_US
dc.language.isoen_USen_US
dc.subjectdesymmetrizationen_US
dc.subjectdenticulatinen_US
dc.subjectchiral lithium amideen_US
dc.titleThe thiopyran route to polypropionates : sequential enantiotopic group selective enolization of meso 1,9-diketonesen_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Saskatchewanen_US
thesis.degree.levelDoctoralen_US
thesis.degree.nameDoctor of Philosophy (Ph.D.)en_US
dc.type.materialtexten_US
dc.type.genreThesisen_US
dc.contributor.committeeMemberAttah-Poku, Samen_US
dc.contributor.committeeMemberPalmer, Daviden_US
dc.contributor.committeeMemberMajewski, Mareken_US
dc.contributor.committeeMemberKerr, Michael A.en_US
dc.contributor.committeeMemberBaranski, Andrzej S.en_US


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