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Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

ABSTRACT: An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

SUBMITTER: Liu Q 

PROVIDER: S-EPMC2684863 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Liu Qin Q   Perreault Stéphane S   Rovis Tomislav T  

Journal of the American Chemical Society 20081004 43

An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates. ...[more]

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