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Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

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Abstract

A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr).

Graphical abstract: Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

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Publication details

The article was received on 21 Nov 2017, accepted on 04 Jan 2018 and first published on 05 Jan 2018


Article type: Letter
DOI: 10.1039/C7NJ04527A
Citation: New J. Chem., 2018, Advance Article
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    Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

    Y. Liu, J. Wang, Z. Wei, J. Cao, D. Liang, Y. Lin and H. Duan, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04527A

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