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dc.contributorDepartment of Applied Biology and Chemical Technologyen_US
dc.creatorChan, Shu-sun-
dc.publisherHong Kong Polytechnic University-
dc.rightsAll rights reserveden_US
dc.titleSynthesis of chiral diphosphine ligands derived from diols and tartaric acid derivative via diastereomeric couplingen_US
dcterms.abstractAsymmetric hydrogenation utilizing molecular hydrogen is one of the most efficient methods for constructing chiral compounds as this method is the simplest, cleanest, efficient, environmentally friendly and economical. It is most widely applied in both industry and academia. This thesis focused on the development of novel C2-symmetric biphenyl diphosphine ligands with chiral linkers and their applications in asymmetric hydrogenations. A C2-symmetric biphenyl diphosphine ligand (R)-[6,6'-(2S',3S'-butadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl 117 with a chiral linker was synthesized. Complete atropdiastereoselectivity was observed in asymmetric intramolecular Ullmann coupling. (S)-[6,6'-(2S',3S'-butadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl 124, (S)-[6,6'-(2R,4R-pentadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl 128 and (S)-[6,6'-(2R,5R-hexadioxy)]-(2,2')-bis(diphenylphosphino)-(1,1')-biphenyl 132 were synthesized via ring closure process. The enantioselectivities of the corresponding Ir and Ru complexes compared well with MeO-BIPHEP 5a. The configuration of the product was controlled by the axial chirality rather than the additional central chirality. Another novel C2-symmetric biphenyl diphosphine ligand, [6,6'-(4S,5S'-2,2-dimethyl-1,3-dioxolane-4,5-dimethoxy)]-(2,2')-bis(diphenylphosphino)-(1,1)-biphenyl 141 and 142 were synthesized via asymmetric Ullmann coupling. However, no atropdiastereoselectivity was observed. The enantioselectivities of the corresponding Ru complexes compared favorably with MeO-BIPHEP 5a. The corresponding Rh complexes showed better enantioselectivities than MeO-BIPHEP 5a. The configuration of product was also controlled by the axial chirality rather than the additional central chirality.en_US
dcterms.extentxx, 187 p. : ill. ; 31 cm.en_US
dcterms.isPartOfPolyU Electronic Thesesen_US
dcterms.educationalLevelAll Doctorateen_US
dcterms.LCSHHong Kong Polytechnic University -- Dissertations.en_US
dcterms.LCSHAsymmetric synthesis.en_US
dcterms.LCSHChiral drugs.en_US
dcterms.accessRightsopen accessen_US

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