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噻吩的催化不对称官能化及去芳构化反应

Catalytic asymmetric functionalization and dearomatization of thiophenes.

作者信息

Zhao Zhengxing, Li Yingxin, Jia Shiqi, Peng Lei, Zhang Zian, Wu Fengdi, Wang Pengfei, Qin Wenling, Lan Yu, Yan Hailong

机构信息

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University Chongqing 401331 P. R. China

Green Catalysis Center, College of Chemistry, Zhengzhou University Zhengzhou 450001 P. R. China

出版信息

Chem Sci. 2024 Aug 2;15(35):14295-303. doi: 10.1039/d4sc03530e.

DOI:10.1039/d4sc03530e
PMID:39156933
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11325187/
Abstract

The asymmetric synthesis of thiophene-derived compounds, including catalytic asymmetric dearomatization of thiophene and atroposelective synthesis of benzothiophene derivatives, has rarely been reported. In this work, the asymmetric transformation of the thiophene motif is investigated. Through the rational design of substrates with a thiophene structure, by using the vinylidene -quinone methide (VQM) intermediate as a versatile tool, axially chiral naphthyl-benzothiophene derivatives and thiophene-dearomatized chiral spiranes were obtained in high yields with excellent enantioselectivities.

摘要

噻吩衍生化合物的不对称合成，包括噻吩的催化不对称去芳构化和苯并噻吩衍生物的阻转选择性合成，鲜有报道。在这项工作中，对噻吩基序的不对称转化进行了研究。通过合理设计具有噻吩结构的底物，利用亚乙烯基 - 醌甲基化物（VQM）中间体这一通用工具，以高收率和优异的对映选择性得到了轴向手性萘基 - 苯并噻吩衍生物和噻吩去芳构化的手性螺环化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/07ed84c837d0/d4sc03530e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/0f1cd1c12ad4/d4sc03530e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/4cb5f32e085b/d4sc03530e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/07ed84c837d0/d4sc03530e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/0f1cd1c12ad4/d4sc03530e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/4cb5f32e085b/d4sc03530e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5853/11389513/07ed84c837d0/d4sc03530e-s3.jpg

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本文引用的文献

1
Modulating the Alkylation Position on Terminal Thiophene Ring of Naphtho[2,3-:6,7-'] Bithieno[2,3-] Thiophene (NBTT) for High-Performance Organic Optoelectronic Devices.调节萘并[2,3-:6,7-']二噻吩并[2,3-]噻吩（NBTT）末端噻吩环上的烷基化位置以用于高性能有机光电器件。
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Enantioselective Synthesis of Atropisomers via Vinylidene -Quinone Methides (VQMs).通过亚乙烯基-醌甲醚（VQMs）对映选择性合成非对映异构体。
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Modular Construction of Heterobiaryl Atropisomers and Axially Chiral Styrenes via All-Carbon Tetrasubstituted VQMs.
通过全碳四取代VQM构建杂芳基阻转异构体和轴手性苯乙烯的模块化结构。
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Atroposelective Construction of Nine-Membered Carbonate-Bridged Biaryls.手性九元环碳酸酯桥联联芳烃的构建。
Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202206501. doi: 10.1002/anie.202206501. Epub 2022 Jun 14.
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Organocatalytic Asymmetric Dearomatizing Hetero-Diels-Alder Reaction of Nonactivated Arenes.有机催化非活化芳烃不对称去芳构化杂 Diels-Alder 反应。
J Am Chem Soc. 2022 Apr 27;144(16):7374-7381. doi: 10.1021/jacs.2c01106. Epub 2022 Apr 13.
6
Organocatalytic Enantioselective Construction of Spiroketal Lactones Bearing Axial and Central Chirality via an Asymmetric Domino Reaction.通过不对称多米诺反应实现具有轴手性和中心手性的螺环内酯的有机催化对映选择性构建。
Org Lett. 2022 Apr 29;24(16):2978-2982. doi: 10.1021/acs.orglett.2c00845. Epub 2022 Apr 5.
7
Asymmetric Azide-Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles.铱（I）/方酰胺协同催化的不对称叠氮化物-炔烃环加成反应：轴手性芳基三唑的对映选择性合成。
J Am Chem Soc. 2022 Apr 13;144(14):6200-6207. doi: 10.1021/jacs.2c02563. Epub 2022 Apr 4.
8
Organocatalytic enantioselective construction of axially chiral (1)-isochromen-1-imines.轴手性(1)-异色烯-1-亚胺的有机催化对映选择性构建
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An Isolable Vinylidene ortho-Quinone Methide: Synthesis, Structure and Reactivity.一种可分离的亚乙烯基邻醌甲基化物：合成、结构与反应活性
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The mechanism and origin of selectivities for NHC-catalyzed synthesis of axially chiral benzothiophene/benzofuran-fused biaryls.NHC 催化合成轴手性苯并噻吩/苯并呋喃稠合联芳基的选择性的机制和起源。
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