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Transition metal-catalyzed asymmetric hydrogenation for synthesis of chiral amines

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TitleInfo
Title
Transition metal-catalyzed asymmetric hydrogenation for synthesis of chiral amines
Name (type = personal)
NamePart (type = family)
Chang
NamePart (type = given)
Mingxin
NamePart (type = date)
1979-
DisplayForm
Mingxin Chang
Role
RoleTerm (authority = RULIB)
author
Name (type = personal)
NamePart (type = family)
Zhang
NamePart (type = given)
Xumu
DisplayForm
Xumu Zhang
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
chair
Name (type = personal)
NamePart (type = family)
Jimenez
NamePart (type = given)
Leslie
DisplayForm
Leslie Jimenez
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Warmuth
NamePart (type = given)
Ralf
DisplayForm
Ralf Warmuth
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Hu
NamePart (type = given)
Longqin
DisplayForm
Longqin Hu
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
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)
2013
DateOther (qualifier = exact); (type = degree)
2013-10
Place
PlaceTerm (type = code)
xx
Language
LanguageTerm (authority = ISO639-2b); (type = code)
eng
Abstract (type = abstract)
Synthesis of chiral amine is one of the major tasks in organic chemistry since chiral amines play important roles in pharmaceutical and agrochemical industry. Among those various methods for chiral amine synthesis, transition metal-catalyzed asymmetric hydrogenation is one of the most efficient asymmetric catalytic technology both on the laboratory and the production scale in synthetic organic chemistry due to its high efficiency and atom economy. In this dissertation, the asymmetric hydrogenation of two types of cyclic imines, direct asymmetric reductive amination and the asymmetric hydrogenation of pyridines were explored for makingof chiral amines. The asymmetric reduction of cyclic imines and N-hereromatic compounds remains a challenge in modern synthesis due to the inhibitory effect from the amine product and the coordination difficulty of the imine substrates to the transition metal center. Our Ir–f-Binaphane catalytic system was proved to be efficient for two types of cyclic imine substrates, 2-arylpyrrolines and dihydroisoquinoline. A ‘green’ method, the direct reductive amination of simple ketones was explored using phenylhydrazide as the nitrogen source. With help of several additives, excellent reactivity (up to 1000 TONs) and enantioselectivities (up to 99% ee) were achieved in iridium–f-Binaphane catalyzed reaction. The direct hydrogenation of pyridines is hard to achieve. The strategy we used is to dearomatize the pyridine ring by addition of an easy-removal protecting group, benzyl, on the nitrogen of pyridines. Collaborating with Merck Catalysis group, and using the neutral iridium–MP2-SegPhos catalytic system, various N-benzyl-2-arylpyridines were hydrogenated under mild condition and high enantioselectivities were achieved.
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_4960
PhysicalDescription
Form (authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
xii, 122 p. : ill.
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
Note (type = statement of responsibility)
by Mingxin Chang
Subject (authority = ETD-LCSH)
Topic
Chirality
Subject (authority = ETD-LCSH)
Topic
Amines--Synthesis
Subject (authority = ETD-LCSH)
Topic
Amines industry
RelatedItem (type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier (type = local)
rucore19991600001
Location
PhysicalLocation (authority = marcorg); (displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier (type = doi)
doi:10.7282/T3HD7SP1
Genre (authority = ExL-Esploro)
ETD doctoral
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Rights

RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Chang
GivenName
Mingxin
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2013-08-26 21:24:24
AssociatedEntity
Name
Mingxin Chang
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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RULTechMD (ID = TECHNICAL1)
ContentModel
ETD
OperatingSystem (VERSION = 5.1)
windows xp
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