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基于硫脲的有机催化剂在不对称多组分反应(AMCRs)中的最新应用。

Recent applications of thiourea-based organocatalysts in asymmetric multicomponent reactions (AMCRs).

机构信息

Department of Chemistry, National Institute of Technology Patna, Ashok Rajpath, Patna - 800005, India.

Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna - 801106, India.

出版信息

Org Biomol Chem. 2020 Jul 29;18(29):5513-5532. doi: 10.1039/d0ob00595a.

Abstract

One-pot multiple bond-forming reactions under metal-free conditions have tremendous potential in organic and medicinal chemistry considering their synthetic efficiency and eco-friendliness. In this direction, organocatalysis, i.e. application of organic molecules as catalysts, in multicomponent reactions is one of the best combinations for the preparation of complex molecules in minimum steps under green reaction conditions. Thiourea-based organic molecules show excellent catalytic activity in various transformations by their unique double H-bonding activation process. Chiral organic molecules having a thiourea backbone are well-recognized catalysts for the enantioselective synthesis of diverse products from asymmetric two- or multicomponent reactions. Simultaneous dual activation of the electrophile and the nucleophile in an MCR by using bifunctional thiourea-based chiral organocatalysts has gained considerable interest in recent times. Although several review articles are available in the literature on organocatalysis, asymmetric domino reactions, or multicomponent reactions using various organocatalysts, however, to date there has been no dedicated review article on this emerging topic, i.e. asymmetric multicomponent reactions catalysed by thiourea-based organocatalysts. Thus, this review aims to highlight the recent applications of thiourea-based organocatalysts in asymmetric multicomponent reactions.

摘要

在无金属条件下进行一锅多键形成反应,考虑到其合成效率和环境友好性,在有机和药物化学中有巨大的潜力。在这一方向上,多组分反应中的有机催化,即有机分子作为催化剂的应用,是在绿色反应条件下以最少的步骤制备复杂分子的最佳组合之一。基于硫脲的有机分子通过其独特的双氢键活化过程,在各种转化中显示出优异的催化活性。具有硫脲骨架的手性有机分子是通过不对称双组分或多组分反应对各种产物进行对映选择性合成的公认的催化剂。最近,使用双功能硫脲基手性有机催化剂同时对 MCR 中的亲电试剂和亲核试剂进行双重活化引起了相当大的兴趣。尽管文献中有几篇关于有机催化、不对称多米诺反应或使用各种有机催化剂的多组分反应的综述文章,但迄今为止,还没有专门针对这一新兴主题的综述文章,即基于硫脲的有机催化剂催化的不对称多组分反应。因此,本综述旨在强调基于硫脲的有机催化剂在不对称多组分反应中的最新应用。

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