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New Mechanism for Cinchona Alkaloid-Catalysis Allows for an Efficient Thiophosphorylation Reaction
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2020-11-12 , DOI: 10.1021/jacs.0c09192
Nastaran Salehi Marzijarani 1 , Yu-hong Lam 2 , Xiao Wang 3 , Artis Klapars 1 , Ji Qi 1, 4 , Zhiyan Song 5 , Benjamin D. Sherry 1 , Zhijian Liu 1 , Yining Ji 1
Affiliation  

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 of the reaction was undertaken, employing a combination of reaction kinetics, NMR spectroscopy, and computational modeling, to better understand the observed reactivity. Taken collectively, the results support an unprecedented mechanism for this class of organocatalyst.

中文翻译:

金鸡纳生物碱催化的新机制允许有效的硫代磷酸化反应

使用金鸡纳生物碱催化剂,在温和的反应条件下,使用市售的硫代磷酰氯高效合成核苷 5'-单硫代磷酸酯。对该反应进行了详细的机理研究,结合了反应动力学、核磁共振光谱和计算模型,以更好地了解观察到的反应性。总的来说,结果支持此类有机催化剂的前所未有的机制。
更新日期:2020-11-12
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