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-2,2,2-三氟乙基异吲哚酮亚胺与不对称二羰基活化烯烃的不对称环加成反应:构建含三个羰基的5'-三氟甲基化3,2'-吡咯烷基螺环氧化吲哚

Asymmetric Cycloaddition of -2,2,2-Trifluoroethylisatin Ketimines and Unsymmetrical Dicarbonyl-Activated Alkenes: Construction of 5'-Trifluoromethylated 3,2'-Pyrrolidinyl Spirooxindoles with Three Carbonyl Groups.

作者信息

He Jin-Zhi, Zhu Bao-Lei, Huang Zhen-Hui, Liang Jin-Ping, Zhang Zhen-Wei, Chen Qing, Lin Ning

机构信息

College of Pharmacy, Guangxi Zhuang Yao Medicine Center of Engineering and Technology, Guangxi University of Chinese Medicine, Nanning 530200, P. R. China.

Guangxi Scientific Research Center of Traditional Chinese Medicine, Guangxi Zhuang Yao Medicine Center of Engineering and Technology, Guangxi University of Chinese Medicine, Nanning, 530200, P. R. China.

出版信息

J Org Chem. 2024 Sep 20;89(18):12924-12934. doi: 10.1021/acs.joc.4c00805. Epub 2024 Aug 28.

DOI:10.1021/acs.joc.4c00805
PMID:39197148
Abstract

The asymmetric cycloaddition between -2,2,2-trifluoroethylisatin ketimines and unsymmetrical dicarbonyl-activated alkenes catalyzed by a bifunctional squaramide has been discovered. The present study demonstrates an efficient approach for the regio-, diastereo-, and enantioselective synthesis of densely functionalized 5'-trifluoromethylated 3,2'-pyrrolidinyl spirooxindoles featuring three different types of carbonyl groups.

摘要

已发现双功能方酰胺催化的-2,2,2-三氟乙基异吲哚酮亚胺与不对称二羰基活化烯烃之间的不对称环加成反应。本研究展示了一种有效方法,用于区域选择性、非对映选择性和对映选择性合成具有三种不同类型羰基的高度官能团化的5'-三氟甲基化3,2'-吡咯烷基螺环氧化吲哚。

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Asymmetric Cycloaddition of -2,2,2-Trifluoroethylisatin Ketimines and Unsymmetrical Dicarbonyl-Activated Alkenes: Construction of 5'-Trifluoromethylated 3,2'-Pyrrolidinyl Spirooxindoles with Three Carbonyl Groups.-2,2,2-三氟乙基异吲哚酮亚胺与不对称二羰基活化烯烃的不对称环加成反应:构建含三个羰基的5'-三氟甲基化3,2'-吡咯烷基螺环氧化吲哚
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