New Mechanism for Cinchona Alkaloid-Catalysis Allows for an Efficient Thiophosphorylation Reaction

• DOI: 10.1021/jacs.0c09192
• Publication Date: 2020-11-12T18:15:17Z
• Authors: Nastaran Salehi M...; Yu-hong Lam; Xiao Wang; Artis Klapars; Ji Qi; Zhiyan Song; Benjamin D. Sherry; Zhijian Liu; Yining Ji
• Keywords: Cinchona; Reactivity

An efficient synthesis of nucleoside 5′-monothiophosphates under mild reaction conditions using commercially available thiophosphoryl chloride was achieved with a cinchona alkaloid catalyst. A detailed mechanistic study the undertaken, employing combination kinetics, NMR spectroscopy, and computational modeling, to better understand observed reactivity. Taken collectively, results support an unprecedented mechanism for this class organocatalyst.