Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates

• Published in: Journal of the American Chemical Society Vol. 130; no. 43; pp. 14066 - 14067
• Main Authors: Liu, Qin, Perreault, Stéphane, Rovis, Tomislav
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 29.10.2008; Amer Chemical Soc
• Subjects: Alkadienes - chemistry; Amides - chemical synthesis; Amides - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Malonates - chemistry; Methane - analogs & derivatives; Methane - chemistry; Molecular Structure; Phenylalanine - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; Sulfonylurea Compounds - chemistry; NUCLEOPHILIC GLYOXYLATION; N-HETEROCYCLIC CARBENE; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY STEREOCENTERS; HYDROBENZOFURANONES; ORGANOCATALYSIS; ALDEHYDES; ACTIVATED DOUBLE-BONDS; NITROALKENES; CYCLOHEXADIENONES
• ISSN: 0002-7863; 1520-5126; 1520-5126
• DOI: 10.1021/ja805680z

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.