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Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.

ABSTRACT: A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

SUBMITTER: Rice GT

PROVIDER: S-EPMC2751616 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.

Rice Grant T GT White M Christina MC

Journal of the American Chemical Society 20090801 33

A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination met ...[more]

PMID: 19645489

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