Application of hydroformylation for the stereoselective synthesis of piperidine alkaloids

• Main Author: Sivarajan Kasinathan
• Other Authors: Roderick Wayland Bates
• Format: Theses and Dissertations
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
• Online Access: https://hdl.handle.net/10356/58924
• Institution: Nanyang Technological University

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.