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糖类的成功:探索基于D-果糖的硫脲作为对映选择性傅克烷基化反应有机催化剂的作用

Saccharide success: exploring the role of d-fructose-based thioureas as organocatalysts for the enantioselective Friedel-Crafts alkylation reaction.

作者信息

Lalhmangaihzuala Samson, Khiangte Vanlalngaihawma, Vanlaldinpuia Khiangte

机构信息

Department of Chemistry, Pachhunga University College, Mizoram University Aizawl 796001 Mizoram India

Department of Chemistry, Mizoram University Tanhril Aizawl 796004 Mizoram India.

出版信息

RSC Adv. 2025 Mar 18;15(11):8335-8345. doi: 10.1039/d5ra00456j. eCollection 2025 Mar 17.

DOI:10.1039/d5ra00456j
PMID:40103969
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11915211/
Abstract

In this study, a series of sixteen (16) d-fructose-based bifunctional thioureas were examined as organocatalysts for the enantioselective Friedel-Crafts alkylation of indoles and pyrrole with β-nitrostyrenes. This investigation is a part of our ongoing project, which aims to expand the scope of application of d-fructose-based thioureas. Under the optimized low-temperature reaction conditions, the corresponding adducts were obtained with good yield (up to 95%) and excellent enantioselectivity (>99% ee).

摘要

在本研究中,考察了一系列十六种(16种)基于d-果糖的双功能硫脲作为吲哚和吡咯与β-硝基苯乙烯对映选择性傅克烷基化反应的有机催化剂。本研究是我们正在进行的项目的一部分,该项目旨在扩大基于d-果糖的硫脲的应用范围。在优化的低温反应条件下,以良好的产率(高达95%)和优异的对映选择性(>99% ee)得到了相应的加合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/5a5d80731057/d5ra00456j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/45579b6f50a8/d5ra00456j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/657ed003e9d9/d5ra00456j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/5a5d80731057/d5ra00456j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/45579b6f50a8/d5ra00456j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/657ed003e9d9/d5ra00456j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81fb/11915211/5a5d80731057/d5ra00456j-f2.jpg

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European J Org Chem. 2023 Jan 2;26(1):e202200950. doi: 10.1002/ejoc.202200950. Epub 2022 Oct 17.
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Recent Advances in the Catalytic Asymmetric Friedel-Crafts Reactions of Indoles.吲哚催化不对称傅克反应的最新进展
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Recent advances in the application of indoles in multicomponent reactions.吲哚在多组分反应中的应用最新进展。
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A chiral bicyclic skeleton-tethered bipyridine-Zn(OTf) complex as a Lewis acid: enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes.手性双环骨架连接联吡啶-Zn(OTf)配合物作为路易斯酸:吲哚与硝基烯烃的不对称 Friedel-Crafts 烷基化反应。
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Enantioselective Friedel-Crafts Alkylation between Nitroalkenes and Indoles Catalyzed by Charge Activated Thiourea Organocatalysts.手性硫脲有机催化剂促进的硝基烯烃与吲哚的不对称 Friedel-Crafts 烷基化反应。
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