Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis,The Journal of Organic Chemistry

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Stereoselective Synthesis of Iminosugar 2-Deoxy(thio)glycosides from Bicyclic Iminoglycal Carbamates Promoted by Cerium(IV) Ammonium Nitrate and Cooperative Brønsted Acid-Type Organocatalysis
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-23 , DOI: 10.1021/acs.joc.0c00324
Irene Herrera-González ₁ , Elena M. Sánchez-Fernández ₁ , Abhijit Sau ₂ , Cristina Nativi ₃ , José M. García Fernández ₄ , M. Carmen Galán ₂ , Carmen Ortiz Mellet ₁

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The first examples of iminosugar-type 2-deoxy(thio)glycoside mimetics are reported. The key step is the activation of a bicyclic iminoglycal carbamate to generate a highly reactive acyliminium cation. Cerium(IV) ammonium nitrate efficiently promoted the formation of 2-deoxy S-glycosides in the presence of thiols, probably by in situ generation of catalytic HNO₃, with complete α-stereoselectivity. Cooperative phosphoric acid/Schreiner’s thiourea organocatalysis proved better suited for generating 2-deoxy O-glycosides, significantly broadening the scope of the approach.

中文翻译：

硝酸铈（IV）铵协同布朗斯台德酸型有机催化双环氨基糖基氨基甲酸酯的立体选择性合成氨基糖2-脱氧（硫）糖苷

报道了亚氨基糖型2-脱氧（硫）糖苷模拟物的第一个实例。关键步骤是激活双环氨基糖基氨基甲酸酯以生成高反应性的酰氨基阳离子。硝酸铈（IV）铵在硫醇存在下有效地促进了2-脱氧S-糖苷的形成，这可能是通过原位生成催化HNO ₃并具有完全的α-立体选择性。磷酸/ Schreiner's硫脲有机催化的协同作用已证明更适合于生成2-脱氧O-糖苷，从而大大拓宽了该方法的范围。

更新日期：2020-03-24

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