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Catalytic Enantioselective O‑Nitrosocarbonyl Aldol Reaction of β‑Dicarbonyl Compounds

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posted on 2012-11-14, 00:00 authored by Mahiuddin Baidya, Kimberly A. Griffin, Hisashi Yamamoto
The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched α-hydroxy-β-ketoesters including the antibacterial natural product kjellmanianone (up to 99% ee). MnO2 was introduced as a mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.