Catalytic enantioselective addition of nitromethane to imines using bisisoquinoline ligands

• Main Author: Fang, Xin
• Other Authors: Zaher Judeh
• Format: Final Year Project
• Language: English
• Published: 2010
• Subjects: DRNTU::Engineering::Chemical engineering::Biochemical engineering
• Online Access: http://hdl.handle.net/10356/38947
• Institution: Nanyang Technological University

The application of bisisoquinolines (BIQ) as catalysts in aza-Henry reactions is relatively new. In this project, bisisoquinoline was prepared from N1, N2-diphenethyloxalamide and polyphosphorous acid. The synthesis process of BIQ was also optimized to give a better yield than literature values. For the aza- Henry reaction, metal salts, solvents used to perform the reaction and different temperatures were optimized. A reaction mechanism was proposed for the reaction based on the experimental findings. HPLC analysis revealed that the enantioselectivity using Boc (tert-butoxyl-carbonyl) protecting group was about 40%. However, better results may be possible with other protecting groups.