The catalytic asymmetric synthesis of CF 3 -containing spiro-oxindole-pyrrolidine-pyrazolone compounds through squaramide-catalyzed 1,3-dipolar cycloaddition

Pharmaceutically important compounds were synthesized through the organocatalytic 1,3-dipolar cycloaddition reaction. In the presence of a cinchonine-derived squaramide catalyst, the cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with α,β-unsaturated pyrazolones gave a spiro-pyrrolidine-lin...

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Veröffentlicht in:Organic & biomolecular chemistry 2019-06, Vol.17 (22), p.5514-5519
Hauptverfasser: Wang, Cui, Wen, Dongwa, Chen, Hui, Deng, Yabo, Liu, Xueting, Liu, Xin, Wang, Li, Gao, Fengyun, Guo, Yifei, Sun, Mengmeng, Wang, Kairong, Yan, Wenjin
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container_issue 22
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container_title Organic & biomolecular chemistry
container_volume 17
creator Wang, Cui
Wen, Dongwa
Chen, Hui
Deng, Yabo
Liu, Xueting
Liu, Xin
Wang, Li
Gao, Fengyun
Guo, Yifei
Sun, Mengmeng
Wang, Kairong
Yan, Wenjin
description Pharmaceutically important compounds were synthesized through the organocatalytic 1,3-dipolar cycloaddition reaction. In the presence of a cinchonine-derived squaramide catalyst, the cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with α,β-unsaturated pyrazolones gave a spiro-pyrrolidine-linked oxindole and pyrazolone compound bearing four consecutive stereocenters and two vicinal spiroquaternary chiral centers, in excellent yields and stereoselectivities.
doi_str_mv 10.1039/C9OB00720B
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title The catalytic asymmetric synthesis of CF 3 -containing spiro-oxindole-pyrrolidine-pyrazolone compounds through squaramide-catalyzed 1,3-dipolar cycloaddition
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