Development of phosphapalladacycles as potential catalysts for asymmetric synthesis

A series of chiral tertiary phosphine ligands have been prepared via two synthetic approaches, namely through the optical resolution of racemic phosphines, and the asymmetric hydrophosphination reaction of enones with secondary phosphines promoted by chiral palladacycles. The ortho-palladation of th...

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Main Author: Chiew, Jun Xuan
Other Authors: Leung Pak Hing
Format: Theses and Dissertations
Language:English
Published: 2017
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Online Access:http://hdl.handle.net/10356/72660
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-726602023-02-28T23:52:11Z Development of phosphapalladacycles as potential catalysts for asymmetric synthesis Chiew, Jun Xuan Leung Pak Hing School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds DRNTU::Science::Chemistry::Inorganic chemistry::Metals A series of chiral tertiary phosphine ligands have been prepared via two synthetic approaches, namely through the optical resolution of racemic phosphines, and the asymmetric hydrophosphination reaction of enones with secondary phosphines promoted by chiral palladacycles. The ortho-palladation of the chiral phosphine ligands resulted in the formation of optically active CP-palladacycles containing a five-membered ring structure. The properties of the newly synthesized phosphapalladacycles were studied by NMR spectroscopy and single crystal X-ray crystallography. The potential use of the phosphapalladacycles as catalysts was explored in the enantioselective addition of various diarylphosphines to benzoquinone for generating P-stereogenic diarylphosphinites readily convertible into various phosphines and their derivatives. ​Doctor of Philosophy (SPMS) 2017-09-06T09:21:02Z 2017-09-06T09:21:02Z 2017 Thesis Chiew, J. X. (2017). Development of phosphapalladacycles as potential catalysts for asymmetric synthesis. Doctoral thesis, Nanyang Technological University, Singapore. http://hdl.handle.net/10356/72660 10.32657/10356/72660 en application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
DRNTU::Science::Chemistry::Inorganic chemistry::Metals
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds
DRNTU::Science::Chemistry::Inorganic chemistry::Metals
Chiew, Jun Xuan
Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
description A series of chiral tertiary phosphine ligands have been prepared via two synthetic approaches, namely through the optical resolution of racemic phosphines, and the asymmetric hydrophosphination reaction of enones with secondary phosphines promoted by chiral palladacycles. The ortho-palladation of the chiral phosphine ligands resulted in the formation of optically active CP-palladacycles containing a five-membered ring structure. The properties of the newly synthesized phosphapalladacycles were studied by NMR spectroscopy and single crystal X-ray crystallography. The potential use of the phosphapalladacycles as catalysts was explored in the enantioselective addition of various diarylphosphines to benzoquinone for generating P-stereogenic diarylphosphinites readily convertible into various phosphines and their derivatives.
author2 Leung Pak Hing
author_facet Leung Pak Hing
Chiew, Jun Xuan
format Theses and Dissertations
author Chiew, Jun Xuan
author_sort Chiew, Jun Xuan
title Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
title_short Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
title_full Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
title_fullStr Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
title_full_unstemmed Development of phosphapalladacycles as potential catalysts for asymmetric synthesis
title_sort development of phosphapalladacycles as potential catalysts for asymmetric synthesis
publishDate 2017
url http://hdl.handle.net/10356/72660
_version_ 1759856782222557184