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从外消旋仲醇对映汇聚式合成手性芴醇：钯（II）/手性降冰片烯协同催化

Enantioconvergent synthesis of chiral fluorenols from racemic secondary alcohols Pd(ii)/chiral norbornene cooperative catalysis.

作者信息

Ding Bo, Xue Qilin, Wei Han, Chen Jiangwei, Liu Ze-Shui, Cheng Hong-Gang, Cong Hengjiang, Tang Jianting, Zhou Qianghui

机构信息

Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences, TaiKang Center for Life and Medical Sciences, Wuhan University Wuhan 430072 China

The Institute for Advanced Studies, Wuhan University Wuhan 430072 China.

出版信息

Chem Sci. 2024 Apr 25;15(21):7975-7981. doi: 10.1039/d4sc01004c. eCollection 2024 May 29.

DOI:10.1039/d4sc01004c
PMID:38817591
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11134410/
Abstract

An efficient protocol for the asymmetric synthesis of fluorenols has been developed through an enantioconvergent process enabled by Pd(ii)/chiral norbornene cooperative catalysis. This approach allows facile access to diverse functionalized chiral fluorenols with constantly excellent enantioselectivities, applying readily available racemic secondary -bromobenzyl alcohols and aryl iodides as the starting materials.

摘要

通过钯（II）/手性降冰片烯协同催化实现的对映汇聚过程，开发了一种高效的芴醇不对称合成方法。该方法以易于获得的外消旋仲溴代苄醇和芳基碘化物为起始原料，能够轻松获得具有始终优异对映选择性的各种功能化手性芴醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/8eff1cfdd2cd/d4sc01004c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/6a8ca14d4872/d4sc01004c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/5562bf809593/d4sc01004c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/8eff1cfdd2cd/d4sc01004c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/6a8ca14d4872/d4sc01004c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/5562bf809593/d4sc01004c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81c5/11134410/8eff1cfdd2cd/d4sc01004c-f2.jpg

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本文引用的文献

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Science. 2023 Oct 27;382(6669):458-464. doi: 10.1126/science.adj0040. Epub 2023 Oct 26.
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Enantioconvergent transformations of secondary alcohols through borrowing hydrogen catalysis.通过借氢催化实现仲醇的对映汇聚式转化。
Chem Soc Rev. 2023 Aug 14;52(16):5541-5562. doi: 10.1039/d3cs00424d.
3
β-Arylation of Racemic Secondary Benzylic Alcohols to Access Enantioenriched β-Arylated Alcohols.
外消旋仲苄醇的β-芳基化反应以获得对映体富集的β-芳基化醇。
Angew Chem Int Ed Engl. 2023 Jul 24;62(30):e202306015. doi: 10.1002/anie.202306015. Epub 2023 Jun 20.
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Catalytic Deracemization Reactions.催化外消旋反应。
J Am Chem Soc. 2023 May 24;145(20):10917-10929. doi: 10.1021/jacs.3c02622. Epub 2023 May 13.
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Synthesis of planar chiral ferrocenes via enantioselective remote C-H activation.通过对映选择性远程 C-H 活化合成平面手性二茂铁。
Nat Chem. 2023 Jun;15(6):815-823. doi: 10.1038/s41557-023-01176-3. Epub 2023 Apr 17.
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Enantioselective Assembly of Ferrocenes with Axial and Planar Chiralities via Palladium/Chiral Norbornene Cooperative Catalysis.通过钯/手性降冰片烯协同催化对具有轴向和平面手性的二茂铁进行对映选择性组装。
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