WEKO3
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Catalytic Bond-Formation Reactions at the γ-Position of β-Ketophosphonates: Asymmetric Mannich Reactions and Formal Aldol Condensation Reactions
https://doi.org/10.15102/0002000896
https://doi.org/10.15102/0002000896a7c5fa30-a86c-443b-a70a-dc12662cd8fd
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OsborneJamesMiloslavColinFulltext.pdf (8.2 MB)
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OsborneJamesMiloslavColinExamAbstract.pdf (68 KB)
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| Item type | 学位論文 / Thesis or Dissertation(1) | |||||||
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| PubDate | 2025-06-16 | |||||||
| Title | ||||||||
| Title | β-ケトホスホネートのγ-位触媒的結合生成反応：不斉マンニッヒ反応および形式アルドール縮合反応 | |||||||
| Language | ja | |||||||
| Title | ||||||||
| Title | Catalytic Bond-Formation Reactions at the γ-Position of β-Ketophosphonates: Asymmetric Mannich Reactions and Formal Aldol Condensation Reactions | |||||||
| Language | en | |||||||
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| Language | eng | |||||||
| Resource Type | ||||||||
| Resource Type Identifier | http://purl.org/coar/resource_type/c_db06 | |||||||
| Resource Type | doctoral thesis | |||||||
| Identifier Registration | ||||||||
| Identifier Registration | 10.15102/0002000896 | |||||||
| Identifier Registration Type | JaLC | |||||||
| Access Right | ||||||||
| Access Rights | open access | |||||||
| Access Rights URI | http://purl.org/coar/access_right/c_abf2 | |||||||
| Author |
Osborne, James Miloslav Colin
× Osborne, James Miloslav Colin
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| Abstract | ||||||||
| Description Type | Abstract | |||||||
| Description | Organocatalytic reactions have been used as an alternative means to enzymatic and organometallic catalysis in accessing functionalized molecules. In this thesis study, organocatalytic regioselective reactions of b-ketophosphonates at the g-position were developed. In the first part, enantioselective g-position-selective Mannich reactions of b ketophosphonates with cyclic sulfonylimines were enabled using 1,3-diamine derivatives and acids as catalysts. 1,3-Diamine derivatives were not previously explored as catalysts, and this study demonstrated the design and use of 1,3-diamine-derived catalysts. In the second part, formal aldol condensation reactions of b-ketophosphonates with arylaldehydes that afford g,d-unsaturated b-ketophosphonates catalyzed by p-anisidine and trifluoroacetic acid were developed. Mechanistic investigations suggest that a Mannich reaction followed by elimination results in the formation of the desired product. Whereas b-ketophosphonates have an active methylene group, in both reactions, g-position-selective C-C bond formations of b-ketophosphonates occurred | |||||||
| Language | en | |||||||
| Exam Date | ||||||||
| 2025-04-04 | ||||||||
| Degree Conferral Date | ||||||||
| Date Granted | 2025-05-31 | |||||||
| Degree | ||||||||
| Degree Name | Doctor of Philosophy | |||||||
| Degree Referral Number | ||||||||
| Dissertation Number | 第193号 | |||||||
| Degree Conferrral Institution | ||||||||
| Degree Grantor Name Identifier Scheme | kakenhi | |||||||
| Degree Grantor Name Identifier | 38005 | |||||||
| Degree Grantor Name | Okinawa Institute of Science and Technology Graduate University | |||||||
| Version Format | ||||||||
| Version Type | VoR | |||||||
| Version Type Resource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||||
| Copyright Information | ||||||||
| Rights | © 2025 The Author. | |||||||
