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DC Field | Value | Language |
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dc.contributor.author | Kaga, Atsushi | en |
dc.date.accessioned | 2018-12-19T13:55:47Z | en |
dc.date.accessioned | 2019-12-06T17:25:29Z | - |
dc.date.available | 2018-12-19T13:55:47Z | en |
dc.date.available | 2019-12-06T17:25:29Z | - |
dc.date.issued | 2018 | en |
dc.identifier.citation | Kaga, A. (2018). Transition metal-free amino-cyclization for the synthesis of saturated azaheterocycles. Doctoral thesis, Nanyang Technological University, Singapore. | en |
dc.identifier.uri | https://hdl.handle.net/10356/89438 | - |
dc.description.abstract | This thesis focused on the development of transition metal-free amino-cyclization towards the synthesis of saturated azaheterocycles and benzannulated saturated azaheterocycles that are ubiquitous scaffolds in biologically active natural products as well as pharmaceuticals. Part 1 of the thesis described alkali metal-mediated amino-cyclization for the synthesis of saturated azaheterocycles and benzannulated saturated azaheterocycles. In Chapter 2, t-BuOK-mediated hydroamination of alkenyl hydrazones was discussed. Modification of the substituents on the hydrazones enabled diastereo-divergent synthesis of 2,5-disubstituted pyrrolidines whereas a unique 2,6-trans selectivity was observed in piperidine formation, which were rationalized by experiments and DFT computation. Chapter 3 described nucleophilic amination of methoxy arenes by means of sodium hydride in the presence of lithium iodide. This protocol served as an efficient route to benzo-fused saturated azaheterocycles as well as aryl amines via intermolecular amination. Mechanistic studies showed that the reaction proceeded through an unprecedented concerted nucleophilic aromatic substitution. In part 2 of the thesis, the author presented total synthesis of (±)-fasicularin having the DNA alkylation ability. The synthesis was stemmed from NBS-mediated spirocyclizing bromoamination of alkenyl azidoester to construct key azaspirocycle. The resulting azaspirocycle was converted to (±)-fasicularin in 14 steps including stereoselective installation of desired hexyl side chain at C(2). Chapter 6 disclosed the experimental and computational data for Chapter 2, 3, and 5. | en |
dc.format.extent | 360 p. | en |
dc.language.iso | en | en |
dc.subject | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis | en |
dc.subject | DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds | en |
dc.title | Transition metal-free amino-cyclization for the synthesis of saturated azaheterocycles | en |
dc.type | Thesis | en |
dc.contributor.supervisor | Chiba Shunsuke | en |
dc.contributor.school | School of Physical and Mathematical Sciences | en |
dc.description.degree | Doctor of Philosophy | en |
dc.identifier.doi | 10.32657/10220/47114 | en |
item.fulltext | With Fulltext | - |
item.grantfulltext | open | - |
Appears in Collections: | SPMS Theses |
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File | Description | Size | Format | |
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1_THESIS_ATSUSHI_KAGA_G1402624E_revised_final.pdf | Thesis | 12.31 MB | Adobe PDF | View/Open |
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