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https://scholarbank.nus.edu.sg/handle/10635/171699
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dc.title | DEVELOPMENT OF A NEW CYCLOHEXYL FUSED SPIRO PHOSPHINE FOR ENANTIOSELECTIVE REACTIONS USING GAMMA-SUBSTITUTED ALLENOATES | |
dc.contributor.author | WU MINGYUE | |
dc.date.accessioned | 2020-07-26T18:00:20Z | |
dc.date.available | 2020-07-26T18:00:20Z | |
dc.date.issued | 2020-01-10 | |
dc.identifier.citation | WU MINGYUE (2020-01-10). DEVELOPMENT OF A NEW CYCLOHEXYL FUSED SPIRO PHOSPHINE FOR ENANTIOSELECTIVE REACTIONS USING GAMMA-SUBSTITUTED ALLENOATES. ScholarBank@NUS Repository. | |
dc.identifier.uri | https://scholarbank.nus.edu.sg/handle/10635/171699 | |
dc.description.abstract | This thesis described the a new type of cyclohexyl fused spirobiindane derived phosphine, NUSIOC-Phos. This bulky catalyst showed high reactivity and enantioselective control in the domino reaction of pyrrolidine-2, 3-diones with gamma-substituted allenoates for the construction of hetero-spirotricyclic lactams. Further studies showed a kinetic resolution was involved in this reaction and many enantiomerically enriched gamma-substituted allenoates were obtained. Secondly, a highly enantiodivergent phosphine catalyzed Michael addition/isomerization and [3+2] annulation for the construction of functionalized 1, 3-conjugated dienes and cyclopentenes was achieved. With NUSIOC-Phos, allenoates reacted smoothly with aroyl acrylate to give a wide range of conjugated 1, 3-dienes. On the other hand, amino acids-based dipeptide phosphine led to the formation of cyclopentene in high yields and high ee. At last, a enantioselective chemodivergent phosphine catalyzed Michael addition and domino process for the construction of functionalized 1,3-conjugated dienes and cyclo-fused bicyclic acetals was developed. NUSIOC-Phos, gamma-substituted allenoates reacted smoothly with tri-carbonyl compounds to furnish a wide range of cyclo-fused bicyclic acetals which are commonly found structural motifs in numerous natural products. It is noteworthy that variation of functional groups from ketones to esters led to a Michael addition/isomerization process, providing functionalized 1, 3-conjugated dienes in high yields and high enantioselectivities. | |
dc.language.iso | en | |
dc.subject | NUSIOCPhos, phosphine catalyst, gamma-lactams, Michael addition, domino reaction | |
dc.type | Thesis | |
dc.contributor.department | CHEMISTRY | |
dc.contributor.supervisor | Yixin Lu | |
dc.description.degree | Ph.D | |
dc.description.degreeconferred | DOCTOR OF PHILOSOPHY (FOS) | |
dc.identifier.orcid | 0000-0002-0577-1707 | |
Appears in Collections: | Ph.D Theses (Open) |
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WUMY.PDF.pdf | 7.56 MB | Adobe PDF | OPEN | None | View/Download |
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