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Molecules 2019, 24(8), 1471; https://doi.org/10.3390/molecules24081471

Asymmetric Henry Reaction of 2-Acylpyridine N-Oxides Catalyzed by a Ni-Aminophenol Sulfonamide Complex: An Unexpected Mononuclear Catalyst

School of Pharmaceutical Science, Chongqing Medical University, Chongqing 400016, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Rafael Chinchilla
Received: 4 April 2019 / Revised: 11 April 2019 / Accepted: 12 April 2019 / Published: 14 April 2019
(This article belongs to the Special Issue Development of Asymmetric Synthesis)
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PDF [1939 KB, uploaded 14 April 2019]
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Abstract

The asymmetric Henry reaction of 2-acylpyridine N-oxide remains a challenge as N-oxides generally act as competitive catalyst inhibitors or displace activating ligands. A novel variable yield (up to 99%) asymmetric Henry reaction of 2-acypyridine N-oxides catalyzed by a Ni-aminophenol sulfonamide complex with good to excellent enantioselectivity (up to 99%) has been developed. Mechanistic studies suggest that the unique properties of the electron-pairs of N-oxides for complexation with Ni makes the unexpected mononuclear complex, rather than the previously reported dinuclear complex, the active species. View Full-Text
Keywords: asymmetric catalysis; Henry reaction; ketones; N-oxides; aminophenol sulfonamide asymmetric catalysis; Henry reaction; ketones; N-oxides; aminophenol sulfonamide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Liu, M.; Gui, D.; Deng, P.; Zhou, H. Asymmetric Henry Reaction of 2-Acylpyridine N-Oxides Catalyzed by a Ni-Aminophenol Sulfonamide Complex: An Unexpected Mononuclear Catalyst. Molecules 2019, 24, 1471.

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