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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkadienes / chemistry*
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Amides / chemical synthesis*
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Amides / chemistry
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Catalysis
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Malonates / chemistry*
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Methane / analogs & derivatives
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Methane / chemistry
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Molecular Structure
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Phenylalanine / chemistry
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Stereoisomerism
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Sulfonylurea Compounds / chemistry*
Substances
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Alkadienes
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Amides
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Malonates
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Sulfonylurea Compounds
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glyoxamide
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carbene
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Phenylalanine
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Methane