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https://scholarbank.nus.edu.sg/handle/10635/50061
DC Field | Value | |
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dc.title | ORGANOCATALYTIC HALOFUNCTIONALIZATION OF OLEFINS | |
dc.contributor.author | TAY WEILIANG DANIEL | |
dc.date.accessioned | 2014-04-10T18:00:13Z | |
dc.date.available | 2014-04-10T18:00:13Z | |
dc.date.issued | 2014-01-08 | |
dc.identifier.citation | TAY WEILIANG DANIEL (2014-01-08). ORGANOCATALYTIC HALOFUNCTIONALIZATION OF OLEFINS. ScholarBank@NUS Repository. | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/50061 | |
dc.description.abstract | Enantioselective halocyclization reactions are important for the synthesis of chiral heterocyclic compounds. In the first part of this thesis, a catalytic enantioselective bromocyclization of olefinic amides has been developed. The resulting enantioenriched 2-substituted 3-bromopiperidines can readily be transformed to 3-substituted piperidines through a silver salt-mediated rearrangement. This process has been applied to the synthesis of a dopaminergic drug, Preclamol. Next, an asymmetric synthesis of heterospirocycles through a double-halocyclization strategy which enabled access to a class of chiral novel spirocycles is reported. In a separate study, the intramolecular chloroamidation of olefinic substrates using diphenyl selenide as the catalyst is developed. The reaction conditions were found to be mild and suitable for a wide range of substrates including those which are acid labile. Lastly, preliminary results for the development of a novel proline-based amino-selenocarbamate catalysts were discussed. A derivative of the catalyst, the amino-selenoether, produced encouraging enantioselectivty for halolactonization reactions. | |
dc.language.iso | en | |
dc.subject | Organocatalyst, Halofunctionalization, Asymmetric, Bromoaminocyclization, Bromoetherification, Chloroamidation | |
dc.type | Thesis | |
dc.contributor.department | NUS GRAD SCH FOR INTEGRATIVE SCI & ENGG | |
dc.contributor.supervisor | CARPENTER, KEITH JOHN | |
dc.contributor.supervisor | YEUNG YING YEUNG | |
dc.description.degree | Ph.D | |
dc.description.degreeconferred | DOCTOR OF PHILOSOPHY | |
dc.identifier.isiut | NOT_IN_WOS | |
Appears in Collections: | Ph.D Theses (Open) |
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TAYWLD.pdf | 10.81 MB | Adobe PDF | OPEN | None | View/Download |
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