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- W2296990651 abstract "This thesis describes, in detail, the synthesis of novel heterobidentate ligands. Theseligands were subsequently used in palladium catalysed allylic substitution reactions tosynthesise enantiomerically enriched alkylated products. The thesis also describesnovel approaches to asymmetric catalysis, in particular asymmetric epoxidationderived from Katsuki-Sharpless methodology.Chapter 1 - This chapter reviews the literature, discussing the significant syntheticadvancements in asymmetric catalysis in the past 10-15 years.Chapter 2 - This chapter describes in detail the synthesis of new heterobidentateligands containing nitrogen and phosphorus ligating atoms. These ligands are basedon imines containing enantiomerically pure asymmetric centres in an alpha position tothe nitrogen moiety. Other ligands that were synthesised were derived from C2-symmetric diamines, also containing an asymmetric centre alpha position to thenitrogen, that produce ligands with the nitrogen functionality contained in a ring.Chapter 3 - This chapter describes the use of the novel ligands synthesised inChapter 2 in palladium catalysed allylic substitution reactions. The racemic substrate,1 ,3-diphenyl-3-acetoxy-1-propene, was alkylated to produce an enantiomeric enrichedalkylated product. The alkylated product was obtained with up to 77 % enantiomericexcess. The reaction was conducted with a palladium catalyst in the presence of anovel ligand using dimethyl malonate as a nucleophile. The development andoptimisation of these ligands within this reaction is discussed.Chapter 4 - This chapter discusses some novel approaches to asymmetricepoxidation. The epoxidation is based on methodology developed by Katsuki andSharpless. This epoxidation relies on the substrate containing an up-unsaturatedalcohol. The chapter discusses the use of a reversible nucleophile in the form ofcyanide. The nucleophile is designed to react with a substrate to provide an upunsaturatedcyanohydrin, suitable to undergo a Katsuki-Sharpless epoxidation. Once the asymmetric epoxidation is complete, the nucleophile would be removed. Thischapter describes the attempts to develop the principle further. An improvement tothe system would be to provide an environment capable of sustaining a dynamickinetic resolution.Chapter 5 - This chapter contains the experimental which provides the exact details ofthe reactions reported in the thesis." @default.
- W2296990651 created "2016-06-24" @default.
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- W2296990651 date "1998-01-01" @default.
- W2296990651 modified "2023-09-27" @default.
- W2296990651 title "Asymmetric catalysis using titanium and palladium" @default.
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- W2296990651 hasPublicationYear "1998" @default.
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