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Title: Design and Applications of Phosphine Ligands to Transition Metal-Catalyzed Reactions
Keywords: phosphine ligands, palladium catalysis, asymmetric addition, transition-metal catalysis, organoboron reagents, cyclic ketimines
Issue Date: 23-Jan-2015
Citation: JIANG CHUNHUI (2015-01-23). Design and Applications of Phosphine Ligands to Transition Metal-Catalyzed Reactions. ScholarBank@NUS Repository.
Abstract: This thesis mainly describes the development of asymmetric palladium catalysis in nucleophilic additions of organoboron reagents to cyclic ketimines to synthesize chiral nitrogen-containing compounds with tertiary carbon center. In addition, this thesis also depicts the attempts of developing new phosphine based ligands derived from amino acids and the preliminary results of their applications in different transition-metal-catalyzed asymmetric reactions. Chapter 1 gave a brief historical background of asymmetric palladium catalysis. The Inventions of three most famous reactions, ?Tsuji?Trost reaction, Mizoroki?Heck reaction and palladium-catalyzed cross-coupling,? were shortly introduced. Beside them, the recent progress of palladium asymmetric addition was also summarized and a selection of examples in this field were described in details, including 1,4-addition, 1,2 addition, cycloaddition and so on. Chapter 2 demonstrated the high performance of palladium-phosphinooxazoline catalyst in asymmetric arylation of cyclic N-sulfonyl ketimines,giving high yields of chiral cyclic sulfonamides which bear tetra-substituted stereogenic center. A systematic comparison between this catalytic system with others was discussed in the main content. Chapter 3 further studied the application of palladium-phosphinooxazoline catalyst in asymmetric addition of organoboron reagents to cyclic trifluoromethyl ketimines. This methodology provided an easy access to anti-HIV drug analogues with potential biological activity. Chapter 4 presented the development of new phosphine based chiral ligands derived from amino acids, including phosphine-amide ligands, phosphine-peptide ligands phosphine-olefin ligands and phosphine-imine ligands. These newly developed ligands were further screened in a series of transition-metal-catalyzed reactions.
Appears in Collections:Ph.D Theses (Open)

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