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postgraduate thesis: Synthesis of aza-bicyclic compounds via palladium-catalyzed cascade cyclization reactions
Title | Synthesis of aza-bicyclic compounds via palladium-catalyzed cascade cyclization reactions |
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Authors | |
Issue Date | 2012 |
Publisher | The University of Hong Kong (Pokfulam, Hong Kong) |
Citation | Lo, K. [羅啟業]. (2012). Synthesis of aza-bicyclic compounds via palladium-catalyzed cascade cyclization reactions. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. Retrieved from http://dx.doi.org/10.5353/th_b4784969 |
Abstract |
A palladium-catalyzed oxidative cascade cyclization reaction has been developed to prepare pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides 2.1ak in one step in moderate to good yields, using Pd(TFA)2 as the catalyst and molecular oxygen (1 atm) as a green oxidant. This cascade cyclization can also proceed for ring-containing unsaturated amides 2.1ln to afford azatricyclic systems.
Palladium(II)-catalyzed dehydrohalogenation cascade cyclization reactions have been developed to synthesize polycyclic pyrrolizidine derivatives from iodoalkenylanilides 4.1ai in satisfactory to excellent yields under mild conditions. This reaction produces two stereocenters in one step and only one single diastereomer was obtained in the cyclization of 4.1. The reaction is proposed to proceed through an organopalladium(IV) species, formed by oxidative addition after the aminopalladation. This organopalladium(IV) species then undergoes reductive elimination to give the cyclized product. This cyclization is a fast and efficient way to construct natural alkaloids that contain pyrrolizidine or indolizidine cores. |
Degree | Doctor of Philosophy |
Subject | Organic cyclic compounds - Synthesis. Palladium catalysts. |
Dept/Program | Chemistry |
Persistent Identifier | http://hdl.handle.net/10722/174527 |
HKU Library Item ID | b4784969 |
DC Field | Value | Language |
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dc.contributor.author | Lo, Kai-yip. | - |
dc.contributor.author | 羅啟業. | - |
dc.date.issued | 2012 | - |
dc.identifier.citation | Lo, K. [羅啟業]. (2012). Synthesis of aza-bicyclic compounds via palladium-catalyzed cascade cyclization reactions. (Thesis). University of Hong Kong, Pokfulam, Hong Kong SAR. Retrieved from http://dx.doi.org/10.5353/th_b4784969 | - |
dc.identifier.uri | http://hdl.handle.net/10722/174527 | - |
dc.description.abstract | A palladium-catalyzed oxidative cascade cyclization reaction has been developed to prepare pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides 2.1ak in one step in moderate to good yields, using Pd(TFA)2 as the catalyst and molecular oxygen (1 atm) as a green oxidant. This cascade cyclization can also proceed for ring-containing unsaturated amides 2.1ln to afford azatricyclic systems. Palladium(II)-catalyzed dehydrohalogenation cascade cyclization reactions have been developed to synthesize polycyclic pyrrolizidine derivatives from iodoalkenylanilides 4.1ai in satisfactory to excellent yields under mild conditions. This reaction produces two stereocenters in one step and only one single diastereomer was obtained in the cyclization of 4.1. The reaction is proposed to proceed through an organopalladium(IV) species, formed by oxidative addition after the aminopalladation. This organopalladium(IV) species then undergoes reductive elimination to give the cyclized product. This cyclization is a fast and efficient way to construct natural alkaloids that contain pyrrolizidine or indolizidine cores. | - |
dc.language | eng | - |
dc.publisher | The University of Hong Kong (Pokfulam, Hong Kong) | - |
dc.relation.ispartof | HKU Theses Online (HKUTO) | - |
dc.rights | The author retains all proprietary rights, (such as patent rights) and the right to use in future works. | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.source.uri | http://hub.hku.hk/bib/B47849691 | - |
dc.subject.lcsh | Organic cyclic compounds - Synthesis. | - |
dc.subject.lcsh | Palladium catalysts. | - |
dc.title | Synthesis of aza-bicyclic compounds via palladium-catalyzed cascade cyclization reactions | - |
dc.type | PG_Thesis | - |
dc.identifier.hkul | b4784969 | - |
dc.description.thesisname | Doctor of Philosophy | - |
dc.description.thesislevel | Doctoral | - |
dc.description.thesisdiscipline | Chemistry | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.5353/th_b4784969 | - |
dc.date.hkucongregation | 2012 | - |
dc.identifier.mmsid | 991033486349703414 | - |