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 poster, will disclose a new asymmetric synthetic method which employs a novel chiral catalyst incorporating a pyridine-N-oxide group as the catalytic site. We investigated several chiral pyridine-N-oxides bearing amino acid-derived chiral auxiliaries for their ability to perform the phosphorylation of a range of alcohols by employing racemic diaryl phosphoryl chlorides. The study involves 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.

Study in the catalytic asymmetric synthesis of optically active organophosphate triesters

253rd National Meeting (2017)

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