Copper-mediated oxidative molecular transformations of N-alkenyl/alkynyl enamine carboxylates for synthesis of azaheterocycles
This thesis describes the Cu-mediated/catalyzed oxidative difunctionalization of C-C unsaturated bonds (cyclopropanation and carbo-oxygenation) of N-alkenyl/alkynyl enamine carboxylates for synthesis of highly functionalized azaheterocycles. The key feature of the present strategy is the single-elec...
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| Format: | Theses and Dissertations |
| Language: | English |
| Published: |
2014
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| Online Access: | http://hdl.handle.net/10356/61954 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | This thesis describes the Cu-mediated/catalyzed oxidative difunctionalization of C-C unsaturated bonds (cyclopropanation and carbo-oxygenation) of N-alkenyl/alkynyl enamine carboxylates for synthesis of highly functionalized azaheterocycles. The key feature of the present strategy is the single-electron-oxidation of an enamine carboxylate by higher valent Cun complex (n = II or III) to give an α-imino carbon radical. Intramolecular addition of the α-imino carbon radical onto the pendent C-C unsaturated bond then constructs an azaheterocyclic radical, which is further functionalized to afford azaheterocycles (3-azabicyclo[3.1.0]hex-2-enes, pyrroles and quinolines). |
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