Home
Resource
Transition metal-catalyzed asymmetric hydrogenation for synthesis of chiral amines
PDF
PDF format is widely accepted and good for printing.
Plug-in required
PDF-1(2.12 MB)
Citation & Export
View Usage Statistics
Staff View

Citation & Export
Hide

Simple citation

Chang, Mingxin. Transition metal-catalyzed asymmetric hydrogenation for synthesis of chiral amines. Retrieved from https://doi.org/doi:10.7282/T3HD7SP1

Export

Click here for information about Citation Management Tools at Rutgers.

Statistics
Hide

Description

TitleTransition metal-catalyzed asymmetric hydrogenation for synthesis of chiral amines
NameChang, Mingxin (author); Zhang, Xumu (chair); Jimenez, Leslie (internal member); Warmuth, Ralf (internal member); Hu, Longqin (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2013
Other Date2013-10 (degree)
SubjectChemistry and Chemical Biology, Chirality, Amines--Synthesis, Amines industry
Extentxii, 122 p. : ill.
DescriptionSynthesis 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.
NotePh.D.
NoteIncludes bibliographical references
Noteby Mingxin Chang
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3HD7SP1
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.
Version 8.5.5
Rutgers University Libraries - Copyright ©2024