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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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
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2017
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| Online Access: | http://hdl.handle.net/10356/72660 |
| _version_ | 1826126605882228736 |
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| author | Chiew, Jun Xuan |
| author2 | Leung Pak Hing |
| author_facet | Leung Pak Hing Chiew, Jun Xuan |
| author_sort | Chiew, Jun Xuan |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T06:55:25Z |
| format | Thesis |
| id | ntu-10356/72660 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:55:25Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-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 |
| 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 |
| title | 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_short | Development of phosphapalladacycles as potential catalysts for asymmetric synthesis |
| title_sort | development of phosphapalladacycles as potential catalysts for asymmetric synthesis |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organometallic compounds DRNTU::Science::Chemistry::Inorganic chemistry::Metals |
| url | http://hdl.handle.net/10356/72660 |
| work_keys_str_mv | AT chiewjunxuan developmentofphosphapalladacyclesaspotentialcatalystsforasymmetricsynthesis |