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Copper-catalyzed enantioselective Mannich reaction between N-acylpyrazoles and isatin-derived ketimines

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Abstract

A copper-catalyzed enantioselective Mannich reaction between N-acylpyrazoles and isatin-derived ketimines is developed. With 5 mol% Cu(CH3CN)4PF6 complexed with 6 mol% chiral amidophosphine ligand L8, 3-substituted 3-amino-2-oxindoles with contiguous stereocenters were produced in 92–99% yields with excellent diastereoselectivities (97 : 3 to 99 : 1 dr) and 94–99% ee under mild conditions.

Graphical abstract: Copper-catalyzed enantioselective Mannich reaction between N-acylpyrazoles and isatin-derived ketimines

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Publication details

The article was received on 29 Apr 2019, accepted on 09 Jun 2019 and first published on 11 Jun 2019


Article type: Research Article
DOI: 10.1039/C9QO00575G
Org. Chem. Front., 2019, Advance Article

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    Copper-catalyzed enantioselective Mannich reaction between N-acylpyrazoles and isatin-derived ketimines

    J. Lu, Y. Fan, F. Sha, Q. Li and X. Wu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00575G

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