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Metal-Free Enantioselective Hydroxyamination of Aldehydes with Nitrosocarbonyl Compounds Catalyzed by an Axially Chiral Amine

Taichi Kano, Fumitaka Shirozu and Keiji Maruoka*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: maruokakuchem.kyoto-u.ac.jp

T. Kano, F. Shirozu, K. Maruoka, J. Am. Chem. Soc., 2013, 135, 17735-17738.

DOI: 10.1021/ja4099627 (free Supporting Information)



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Abstract

A highly regio- and enantioselective hydroxyamination of aldehydes with in situ generated nitrosocarbonyl compounds from hydroxamic acid derivatives was realized by combining TEMPO and BPO as oxidants in the presence of a binaphthyl-modified amine catalyst.

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Key Words

α-amination, β-amino alcohols, hydroxylamines, benzoyl peroxide, TEMPO, sodium borohydride, organocatalysis


ID: J48-Y2013