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Design and synthesis of chiral ligands and their application in transition metal-catalyzed asymmetric hydrogenations

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Title
Design and synthesis of chiral ligands and their application in transition metal-catalyzed asymmetric hydrogenations
Name (type = personal)
NamePart (type = family)
Liu
NamePart (type = given)
Shaodong
NamePart (type = date)
1990-
DisplayForm
Shaodong Liu
Role
RoleTerm (authority = RULIB)
author
Name (type = personal)
NamePart (type = family)
Zhang
NamePart (type = given)
Xumu
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Xumu Zhang
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Advisory Committee
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chair
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Jimenez
NamePart (type = given)
Leslie
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Leslie Jimenez
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Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
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Goldman
NamePart (type = given)
Alan
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Alan Goldman
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Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Hu
NamePart (type = given)
Longqin
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Longqin Hu
Affiliation
Advisory Committee
Role
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outside member
Name (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB)
degree grantor
Name (type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm (authority = RULIB)
school
TypeOfResource
Text
Genre (authority = marcgt)
theses
OriginInfo
DateCreated (qualifier = exact)
2016
DateOther (qualifier = exact); (type = degree)
2016-10
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2016
Place
PlaceTerm (type = code)
xx
Language
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eng
Abstract (type = abstract)
Transition 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.
Subject (authority = RUETD)
Topic
Chemistry and Chemical Biology
RelatedItem (type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier (type = RULIB)
ETD
Identifier
ETD_7481
PhysicalDescription
Form (authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
1 online resource (xvi, 131 p. : ill.)
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
Subject (authority = ETD-LCSH)
Topic
Hydrogenation
Note (type = statement of responsibility)
by Shaodong Liu
RelatedItem (type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier (type = local)
rucore19991600001
Location
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NjNbRU
Identifier (type = doi)
doi:10.7282/T3RV0R13
Genre (authority = ExL-Esploro)
ETD doctoral
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RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Liu
GivenName
Shaodong
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2016-08-11 23:03:54
AssociatedEntity
Name
Shaodong Liu
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
AssociatedObject
Type
License
Name
Author Agreement License
Detail
I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
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