New Mechanism for Cinchona Alkaloid-Catalysis Allows for an Efficient Thiophosphorylation Reaction,Journal of the American Chemical Society

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New Mechanism for Cinchona Alkaloid-Catalysis Allows for an Efficient Thiophosphorylation Reaction
Journal of the American Chemical Society ( IF 14.4 ) 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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