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Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis

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Abstract

The enantioselective nitro-Mannich reaction of unactivated ketone-derived imines (ketimines) has long been a challenge. With the introduction of the protecting group 6-methyl-2-pyridylsulfonyl to the ketimines, this challenging reaction was performed successfully by using a novel bifunctional quaternary ammonium salt bearing a thiourea group derived from quinine, and when relatively small quantities of nitroalkanes were used, the corresponding products were obtained in good to high yields with high enantioselectivities (up to 93% ee). Density functional theory (DFT) calculations are also performed to give the possible transition-state model.

Graphical abstract: Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis

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Publication details

The article was received on 14 Feb 2017, accepted on 16 Mar 2017 and first published on 20 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00124J
Citation: Org. Chem. Front., 2017, Advance Article
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    Highly enantioselective nitro-Mannich reaction of ketimines under phase-transfer catalysis

    B. Wang, T. Xu, L. Zhu, Y. Lan, J. Wang, N. Lu, Z. Wei, Y. Lin and H. Duan, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00124J

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