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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.

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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