Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.
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.
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Qin
Q
Liu
Stéphane
S
Perreault
Tomislav
T
Rovis
D000466:Alkadienes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008314:Malonates / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry; D013237:Stereoisomerism; D013453:Sulfonylurea Compounds / Q000737:chemistry*
D000466:Alkadienes; D000577:Amides; D008314:Malonates; D013453:Sulfonylurea Compounds; C032160:glyoxamide; C030011:carbene; D010649:Phenylalanine; D008697:Methane