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六元螺环氧化吲哚的合成——一种手性布朗斯特酸催化的不对称分子内傅克反应。

Synthesis of six-membered spirooxindoles a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction.

作者信息

Chen Hui-Xuan, Zhang Yaqi, Zhang Yuyang, He Xuefeng, Zhang Zhen-Wei, Liang Hao, He Wenhuan, Jiang Xiaoding, Chen Xiangmeng, Qiu Liqin

机构信息

School of Chemistry, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Sun Yat-Sen University No. 135 Xingangxi Road Guangzhou 510275 People's Republic of China

College of Pharmacy, Guangxi University of Chinese Medicine Nanning 530200 People's Republic of China.

出版信息

RSC Adv. 2018 Nov 1;8(65):37035-37039. doi: 10.1039/c8ra06710d.

DOI:10.1039/c8ra06710d
PMID:35557774
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9089239/
Abstract

By means of the direct condensation of -aminoethylpyrroles and isatins, followed by a chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction, a new class of valuable chiral 3',4'-dihydro-2'-spiro[indoline-3,1'-pyrrolo[1,2-]pyrazin]-2-ones bearing a quaternary carbon stereocenter were successfully synthesized in good to excellent yields and with moderate to good enantioselectivities under mild reaction conditions.

摘要

通过α-氨基乙基吡咯与异吲哚酮的直接缩合,随后在手性磷酸催化下进行不对称分子内傅克反应,在温和的反应条件下,以良好至优异的产率和中等至良好的对映选择性成功合成了一类新型的具有季碳立体中心的有价值的手性3',4'-二氢-2'-螺[吲哚啉-3,1'-吡咯并[1,2 -]吡嗪]-2-酮。

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本文引用的文献

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Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides.双金属接力催化吡啶叶立德环加成反应不对称合成四氢中氮茚
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12323-12327. doi: 10.1002/anie.201806630. Epub 2018 Aug 27.
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Catalytic asymmetric synthesis of spirooxindoles: recent developments.手性催化螺环吲哚的合成:最新进展。
Chem Commun (Camb). 2018 Jun 19;54(50):6607-6621. doi: 10.1039/c8cc02364f.
3
Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles.
用于合成螺环氧化吲哚的不对称催化双迈克尔加成反应
Chemistry. 2018 Mar 12;24(15):3703-3706. doi: 10.1002/chem.201800043. Epub 2018 Feb 19.
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Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N'-Dioxide-Metal Complexes.手性 N,N'-二氧代合金属配合物催化的不对称环加成和环化反应。
Acc Chem Res. 2017 Oct 17;50(10):2621-2631. doi: 10.1021/acs.accounts.7b00377. Epub 2017 Oct 2.
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Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide free carbene.镍(II)催化3-烯基氧化吲哚与苯碘叶立德游离卡宾的对映选择性环丙烷化反应。
Chem Sci. 2016 Apr 21;7(4):2717-2721. doi: 10.1039/c5sc03658e. Epub 2016 Jan 4.
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Discovery of 4-((3'R,4'S,5'R)-6″-Chloro-4'-(3-chloro-2-fluorophenyl)-1'-ethyl-2″-oxodispiro[cyclohexane-1,2'-pyrrolidine-3',3″-indoline]-5'-carboxamido)bicyclo[2.2.2]octane-1-carboxylic Acid (AA-115/APG-115): A Potent and Orally Active Murine Double Minute 2 (MDM2) Inhibitor in Clinical Development.4-((3'R,4'S,5'R)-6″-氯-4'-(3-氯-2-氟苯基)-1'-乙基-2″-氧代二螺[环己烷-1,2'-吡咯烷-3',3″-吲哚啉]-5'-甲酰胺基)双环[2.2.2]辛烷-1-羧酸(AA-115/APG-115)的发现:一种正在临床开发中的强效口服活性小鼠双微体2(MDM2)抑制剂。
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