Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids
This thesis describes the advantages of hydroformylation, when incorporated into natural product synthesis as well as, flow chemistry. The first chapter gives a brief overview of application of hydroformylation in natural product synthesis. It highlights the importance of hydroformylation as a tool...
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| Format: | Thesis |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/58924 |
| _version_ | 1811697705965060096 |
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| author | Sivarajan Kasinathan |
| author2 | Roderick Wayland Bates |
| author_facet | Roderick Wayland Bates Sivarajan Kasinathan |
| author_sort | Sivarajan Kasinathan |
| collection | NTU |
| description | This thesis describes the advantages of hydroformylation, when incorporated into natural product synthesis as well as, flow chemistry. The first chapter gives a brief overview of application of hydroformylation in natural product synthesis. It highlights the importance of hydroformylation as a tool for formation of a new carbon-carbon bond and its capability of introducing reactive aldehyde functional groups. The second and third chapters describe the synthesis of pseudoconhydrine and azimic acid using a common methodology that incorporates hydroformylation, for a simple yet efficient stereoselective synthesis of these types of piperidine alkaloids. The fourth chapter explores the advantages of application of hydroformylation in flow chemistry. It discusses the improvement in the safety profile, the simplification in the experimental procedures and the efficient synthesis of styrenes as compared to batch chemistry. The fifth chapter explores the possibilities of inducing a 1,2-alkyl shift in 2,3,6-trisubstituted piperidines. |
| first_indexed | 2024-10-01T07:59:31Z |
| format | Thesis |
| id | ntu-10356/58924 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:59:31Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/589242023-02-28T23:56:25Z Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids Sivarajan Kasinathan Roderick Wayland Bates School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis This thesis describes the advantages of hydroformylation, when incorporated into natural product synthesis as well as, flow chemistry. The first chapter gives a brief overview of application of hydroformylation in natural product synthesis. It highlights the importance of hydroformylation as a tool for formation of a new carbon-carbon bond and its capability of introducing reactive aldehyde functional groups. The second and third chapters describe the synthesis of pseudoconhydrine and azimic acid using a common methodology that incorporates hydroformylation, for a simple yet efficient stereoselective synthesis of these types of piperidine alkaloids. The fourth chapter explores the advantages of application of hydroformylation in flow chemistry. It discusses the improvement in the safety profile, the simplification in the experimental procedures and the efficient synthesis of styrenes as compared to batch chemistry. The fifth chapter explores the possibilities of inducing a 1,2-alkyl shift in 2,3,6-trisubstituted piperidines. DOCTOR OF PHILOSOPHY (SPMS) 2014-04-14T07:09:14Z 2014-04-14T07:09:14Z 2014 2014 Thesis Sivarajan Kasinathan. (2014). Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/58924 10.32657/10356/58924 en 362 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Sivarajan Kasinathan Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title | Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title_full | Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title_fullStr | Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title_full_unstemmed | Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title_short | Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| title_sort | application of hydroformylation for the stereoselective synthesis of piperidine alkaloids |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/58924 |
| work_keys_str_mv | AT sivarajankasinathan applicationofhydroformylationforthestereoselectivesynthesisofpiperidinealkaloids |