2‐Chloroimidazolium Chloride as a Coupling Reagent for Amide Bond Formation,ChemistrySelect

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2‐Chloroimidazolium Chloride as a Coupling Reagent for Amide Bond Formation
ChemistrySelect ( IF 1.9 ) Pub Date : 2020-04-20 , DOI: 10.1002/slct.202000391
Jie Han _{1,

2} , Yingjie Sun _{1,

2} , Zhifan Wang ₃ , Qingfei Huang ₁ , Jin Zhu ₁ , Yuanhua Wang ₃ , Liu Zhong ₄ , Qiwei Wang _{1,

4}

Affiliation

A highly efficient synthesis strategy, focusing on amide bond formation and peptide synthesis, has been developed under mild condition by employing a 2‐chloroimidazolium chloride IMesCl−Cl as a coupling reagent. This strategy exhibited wide substrate scope and good chemo‐selectivity. Notably, no significant loss of enantiopurity was observed when employing this strategy to dipeptide synthesis. This method was also successfully applied in glycine‐conjugate bile acids synthesis. A plausible formation mechanism via an active ester intermediate was proposed.

中文翻译：

2-氯咪唑鎓氯化物作为酰胺键形成的偶联剂

在温和条件下，通过使用2-氯咪唑鎓氯化物IMesCl-Cl作为偶联剂，已经开发了一种高效的合成策略，重点是酰胺键的形成和肽的合成。该策略具有广泛的底物范围和良好的化学选择性。值得注意的是，当采用这种策略进行二肽合成时，没有观察到对映体纯度的明显损失。该方法也成功地应用于甘氨酸-胆汁酸的合成中。提出了通过活性酯中间体的合理的形成机理。

更新日期：2020-04-22

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