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Biomimetic Clauson‐Kass and Paal‐Knorr Pyrrole Synthesis Using β‐Cyclodextrin‐SO3H under Aqueous and Neat Conditions ‐ Application to Formal Synthesis of Polygonatine†
ChemistrySelect ( IF 2.1 ) Pub Date : 2018-09-11 , DOI: 10.1002/slct.201801559
Rani N. Patil 1 , A. Vijay Kumar 1
Affiliation  

The synthesis of pyrroles under mild conditions using sulfonic acid‐functionalized β‐Cyclodextrin (β‐CD) as a supramolecular catalyst under aqueous conditions is demonstrated. Good to excellent conversion of various amines into pyrroles was observed without any side product formation. CD was found to play a dual role as a phase transfer reagent through inclusion as well as an acid catalyst thereby facilitating the smooth conversions of reactants. The advantages of this protocol are mild reaction conditions, sustainable catalyst and use of non‐toxic solvent water. Notably, the catalyst can be easily recovered and reused up to five cycles without any loss of catalytic activity. The developed protocol was successfully used as a key step for the formal synthesis of the alkaloid natural product Polygonatine.

中文翻译:

在水性和纯净条件下使用β-环糊精-SO3H仿生克劳森-卡斯和帕尔-克诺尔吡咯合成法-用于多哥纳汀的形式合成†

使用磺酸功能化的β-环糊精(β)在温和条件下合成吡咯‐CD)在水性条件下作为超分子催化剂被证明。观察到各种胺良好至优异地转化为吡咯,而没有任何副产物形成。发现CD通过包含以及作为酸催化剂而起相转移试剂的双重作用,从而促进反应物的平滑转化。该协议的优点是反应条件温和,催化剂可持续且使用无毒溶剂水。值得注意的是,该催化剂可以容易地回收并重复使用多达五个循环,而没有任何催化活性的损失。所开发的方案已成功用作生物碱天然产物Polygonatine正式合成的关键步骤。
更新日期:2018-09-11
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