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Issue 18, 2018
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An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons

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Abstract

An organocatalyzed asymmetric Mannich reaction of pyrazoleamides and cyclic trifluoromethyl ketimines with a chiral bifunctional amine-squaramide as the catalyst was developed. A wide range of trifluoromethyl dihydroquinazolinone derivatives bearing adjacent quaternary and tertiary stereogenic centers were readily obtained in good to excellent yields (up to 99%) with high diastereo- and enantioselectivities (up to 99% ee and >20 : 1 dr). The large scale experiment and transformation of the product have also been demonstrated.

Graphical abstract: An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons

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Publication details

The article was received on 23 Mar 2018, accepted on 16 Apr 2018 and first published on 16 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00707A
Citation: Org. Biomol. Chem., 2018,16, 3372-3375
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    An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons

    Y. Luo, K. Xie, D. Yue, X. Zhang, X. Xu and W. Yuan, Org. Biomol. Chem., 2018, 16, 3372
    DOI: 10.1039/C8OB00707A

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