Studies in the Catalytic Asymmetric Synthesis of Optically Active Organophosphate Triesters

• Main Author: Wei, Tzyh-Mann
• Format: Dissertation
• Language: English
• Published: ProQuest Dissertations & Theses 01.01.2018
• Subjects: Organic chemistry
• ISBN: 9780438196216; 043819621X

Chiral organophosphates and derivatives play a significant role in many areas, being employed as organocatalysts, agrochemicals and drugs. In many of these cases, the enantiopurity of the organophosphate ester or derivative is a central issue for their function as catalysts or effectiveness as biologically relevant compounds. To date, there has not been developed an efficient and general catalyst system that accomplishes the asymmetric synthesis of organophosphate triesters. In this project, we will disclose our studies in two new asymmetric synthetic methods. First, we employ a novel chiral catalyst incorporating a pyridine-N-oxide group as the catalytic site. Second, a chiral Lewis acid, Mg coordinated with chiral ligands, as the catalyst will be examined in the asymmetric phosphorylation of alcohols. The studies will involve examining effects on the catalytic efficiency due to temperature variations, solvent effects, and the influence of additional additives. The relationship between these factors as well as the catalyst and the phosphoryl chloride structure on the observed asymmetric induction will be discussed.