Copper-mediated oxidative molecular transformations of N-alkenyl/alkynyl enamine carboxylates for synthesis of azaheterocycles

• Main Author: Toh, Kah Kah
• Other Authors: Chiba Shunsuke
• Format: Theses and Dissertations
• Language: English
• Published: 2014
• Subjects: DRNTU::Science
• Online Access: http://hdl.handle.net/10356/61954
• Institution: Nanyang Technological University

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).