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Catalytic enantioselective O-nitrosocarbonyl aldol reaction of ?-dicarbonyl compounds.

ABSTRACT: The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched ?-hydroxy-?-ketoesters including the antibacterial natural product kjellmanianone (up to 99% ee). MnO(2) was introduced as a mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

SUBMITTER: Baidya M

PROVIDER: S-EPMC3515642 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Catalytic enantioselective O-nitrosocarbonyl aldol reaction of β-dicarbonyl compounds.

Baidya Mahiuddin M Griffin Kimberly A KA Yamamoto Hisashi H

Journal of the American Chemical Society 20121102 45

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). MnO(2) was introduced as a mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives. ...[more]

PMID: 23106266

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