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基于生物碱骨架的新型硒脲:合成与催化研究

Novel Selenoureas Based on Alkaloid Skeleton: Synthesis and Catalytic Investigations.

作者信息

Zielińska-Błajet Mariola, Najdek Joanna

机构信息

Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland.

Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.

出版信息

Materials (Basel). 2021 Jan 28;14(3):600. doi: 10.3390/ma14030600.

DOI:10.3390/ma14030600
PMID:33525376
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7866029/
Abstract

An efficient approach to the synthesis of chiral selenoureas consisting of alkaloid scaffolds was described. The new selenoureas were assessed as bifunctional organocatalysts in the asymmetric Michael addition reactions under mild conditions. The best results were obtained for selenoureas bearing the 4-fluorophenyl group. These catalysts promoted the reactions with enantioselectivities of up to 96% ee. Additionally, the catalytic performance of the thiourea and selenourea counterpart was compared.

摘要

描述了一种合成由生物碱骨架组成的手性硒脲的有效方法。在温和条件下,将新型硒脲作为双功能有机催化剂用于不对称迈克尔加成反应中进行评估。对于带有4-氟苯基的硒脲,获得了最佳结果。这些催化剂促进反应的对映选择性高达96%ee。此外,还比较了硫脲和硒脲对应物的催化性能。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e062/7866029/75e0e31fb3a4/materials-14-00600-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e062/7866029/4da6dbd00e8e/materials-14-00600-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e062/7866029/75e0e31fb3a4/materials-14-00600-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e062/7866029/4da6dbd00e8e/materials-14-00600-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e062/7866029/75e0e31fb3a4/materials-14-00600-g001.jpg

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Org Biomol Chem. 2020 Jul 29;18(29):5513-5532. doi: 10.1039/d0ob00595a.
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Bis-Selenoureas for Anion Binding: A 1H NMR and Theoretical Study.双硒脲衍生物对阴离子的结合作用:1H NMR 和理论研究。
Chempluschem. 2020 Jul;85(7):1389-1395. doi: 10.1002/cplu.202000260.
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Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.手性硫脲——在不对称合成和药物化学中的制备及意义。
Molecules. 2020 Jan 18;25(2):401. doi: 10.3390/molecules25020401.
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Antioxidants (Basel). 2020 Jan 8;9(1):55. doi: 10.3390/antiox9010055.
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Antimicrob Agents Chemother. 2019 Apr 25;63(5). doi: 10.1128/AAC.02200-18. Print 2019 May.
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