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Ruoyu Ma Dissertation.pdf (10.12 MB)

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Chiral NHC-Au(I) Catalyzed Enantioselective Reactions

Ma, Ruoyu
http://orcid.org/0000-0001-9636-7365
http://rave.ohiolink.edu/etdc/view?acc_num=miami1585432603722902

Abstract Details

2020, Doctor of Philosophy, Miami University, Chemistry and Biochemistry.
Homogenous gold catalysts are versatile tools in organic synthesis due to their strong ability to form new C-C bonds or C-heteratom bonds. The asymmetric version of the gold catalysts are developed much slower due to the linear coordination property of the Au(I) atom. This property makes the reaction site far away from the chiral ligand. Most chiral ligands developed for gold catalysis are phosphine ligands. N-hetercyclic carbene(NHC) ligand has its own advantages over the phosphine ligand. The chiral NHC ligands developed by our group are large enough to reach to the reaction center to achieve enantioselectivity with the biphenyl moieties. We have designed and synthesized a series of chiral NHC-Au(I) catalysts with bulky substituents on the NHC ligand. All the gold complexes have been identified by 1H, 13C NMR spectroscopy. Several gold complexes have been identified by X-ray single crystal structure analysis. The activated gold catalysts have been applied to both asymmetric [4+3] cycloaddition reactions and asymmetric 1, 6-enyne cyclization. The cycloaddition product has been identified with X-ray single crystal structure analysis. The enantioselectivity of the asymmetric [4+3] cycloaddition has reached 89% ee. The absolute configuration of the major enantiomer has been deduced by a combination of X-ray single crystal structure analysis, NMR and DFT study.
Benjamin Gung (Advisor)
Richard Taylor (Committee Chair)
David Tierney (Committee Member)
Dominik Konkolewicz (Committee Member)
John Rakovan (Committee Member)
203 p.
Organic Chemistry

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Citations

  • Ma, R. (2020). Chiral NHC-Au(I) Catalyzed Enantioselective Reactions [Doctoral dissertation, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1585432603722902

    APA Style (7th edition)

  • Ma, Ruoyu. Chiral NHC-Au(I) Catalyzed Enantioselective Reactions. 2020. Miami University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1585432603722902.

    MLA Style (8th edition)

  • Ma, Ruoyu. "Chiral NHC-Au(I) Catalyzed Enantioselective Reactions." Doctoral dissertation, Miami University, 2020. http://rave.ohiolink.edu/etdc/view?acc_num=miami1585432603722902

    Chicago Manual of Style (17th edition)

miami1585432603722902
115
© 2020, some rights reserved.Creative Commons License Chiral NHC-Au(I) Catalyzed Enantioselective Reactions by Ruoyu Ma is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by Miami University and OhioLINK.