Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/13746
Title: Synthesis and application of stereoisomeric coordination compounds
Authors: NG KHIM HUI
Keywords: cyclopalladated-amine, catalysts, asymmetric Claisen rearrangement, chiral template, asymmetric Diels-Alder, cycloadduct
Issue Date: 4-Mar-2004
Source: NG KHIM HUI (2004-03-04). Synthesis and application of stereoisomeric coordination compounds. ScholarBank@NUS Repository.
Abstract: The cyclopalladated-amine complexes have played an important role in synthetic stereochemistry. Among the many applications are enantiomeric discrimination, chiral shift reagent, clear and reliable references for NMR assignment of unknown absolute configurations, as well as excellent chiral templates for the asymmetric Diels-Alder reaction between 3,4-dimethyl-1-phenylphosphole (DMPP) and a range of dienophiles. However, the function of the cyclopalladated-amine complexes has not been fully explored. Thus, a series of cyclopalladated-amine complexes were studied as catalysts in the asymmetric Claisen rearrangement. The results showed that all complexes, except (-)-bis(acetonitrile)[(R)-9-(1-(dimethylamino)ethyl-10-phenan-threnyl)-C,N]-palladium (II) perchlorate, catalyzed both unactivated and activated substrate. (S,S)-di-i?--chlorobis[9-[(1-dimethylamino)ethyl]-10-phenanthrenyl-C,N]-dipalladium was found to be the most enantioselective catalyst among all the complexes being studied. Other than the application in catalysis, (S, S)-di-i?--chlorobis[9-[(1-dimethylamino)ethyl]-10-phenanthrenyl-C,N]dipalladium (II) was also found to be an effective chiral template in promoting asymmetric Diels-Alder reaction between 1-phenyl-3,4-dimethylphosphole and N, Na??-dimethyl-trans-4-oxo-2-pentenamide, in which only one diastereomeric cycloadduct was produced.
URI: http://scholarbank.nus.edu.sg/handle/10635/13746
Appears in Collections:Ph.D Theses (Open)

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Summary.PDF35.82 kBAdobe PDF

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References.PDF64.27 kBAdobe PDF

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Appendix_2.PDF249.32 kBAdobe PDF

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