Nitrogen heterocycles via palladium-catalyzed carbocyclization. Formal synthesis of (+)-alpha-allokainic acid.
[reaction: see text] The Pd-catalyzed carbocyclization of ketoamides was investigated and found to be highly dependent on the phosphine ligand as well as the presence of coordinating counterions. Nitrogen heterocycles were formed without erosion of the stereochemical integrity. The utility of the lactam products was demonstrated by the formal synthesis of (+)-alpha-allokainic acid.
Cook
Gregory R
GR
Center for Protease Research, Department of Chemistry and Molecular Biology, North Dakota State University, P.O. Box 5516, Fargo, North Dakota 58105-5516, USA. gregory.cook@ndsu.nodak.edu
Sun
Liangdong
L
D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D007608:Kainic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010720:Phosphines; C495695:allokainic acid; D010165:Palladium; D009584:Nitrogen; D007608:Kainic Acid