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Design and synthesis of chiral ligands and their application in transition metal-catalyzed asymmetric hydrogenations
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Liu, Shaodong. Design and synthesis of chiral ligands and their application in transition metal-catalyzed asymmetric hydrogenations. Retrieved from https://doi.org/doi:10.7282/T3RV0R13

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TitleDesign and synthesis of chiral ligands and their application in transition metal-catalyzed asymmetric hydrogenations
NameLiu, Shaodong (author); Zhang, Xumu (chair); Jimenez, Leslie (internal member); Goldman, Alan (internal member); Hu, Longqin (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2016
Other Date2016-10 (degree)
SubjectChemistry and Chemical Biology, Hydrogenation
Extent1 online resource (xvi, 131 p. : ill.)
DescriptionTransition metal catalyzed hydrogenations are among the most powerful and direct approaches for the synthesis of organic molecules. During the past half century, chiral ligands have been extensively studied in transition metal catalyzed transformations. Development of new chiral ligands, efficient catalyst systems and their applications in the reduction of various prochiral unsaturated substrates are the focus of this dissertation. In chapter 1, novel chiral tridentate f-amphox ligands were designed and synthesized. Two chiral wings in the ligands form a chiral pocket which introduces the chirality in the asymmetric hydrogenation. Tridentate f-amphox ligand has formed a highly enantioselective Iridium catalyst for direct hydrogenation of β-aryl β-ketoesters (up to 99% ee) and 3-oxo-3-arylpropionic acid ethyl esters (up to 99% ee) with high turnover number (up to 1,000,000). In chapter 2, I focus on the highly enantioselective direct reductive amination of aromatic ketone. With phenylhydrazide as the nitrogen source, various chiral hydrazides were synthesized in excellent enantioselectivities and yields. In chapter 3, a highly efficient enantioselective hydrogenation of N-alkyl-2-arylpyridinium salts was discussed. This work provides the unique example of using a chiral phosphole-based ligand for highly efficient asymmetric catalysis. The mechanism of this transformation was studied and a mechanistic cycle was proposed.
NotePh.D.
NoteIncludes bibliographical references
Noteby Shaodong Liu
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3RV0R13
Languageeng
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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