Enantioselective Oxidative Coupling of β‑Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis

Enantioselective Oxidative Coupling of β‑Ketocarbonyls and Anilines by Joint Chiral Primary Amine and Selenium Catalysis

An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-h...

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Bibliographic Details
Published in:Organic letters Vol. 21; no. 20; pp. 8178 - 8182
Main Authors: Chen, Wanting, Wang, Yanni, Mi, Xueling, Luo, Sanzhong
Format: Journal Article
Language:English
Published: United States American Chemical Society 18-10-2019
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Summary:An enantioselective primary amine-catalyzed total N-selective nitroso aldol reaction (N-NA) was achieved through the oxidation of primary aromatic amines to the corresponding nitrosoarenes catalyzed by selenium reagents and 30% H2O2. This protocol provides a facile and highly efficient access to α-hydroxyamino carbonyls bearing chiral quaternary centers under exceedingly mild and green reaction conditions with high chemo- and enantiocontrol.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02636