Aluminum chloride-mediated kinetic resolution of racemic gamma-substituted-gamma-lactones.
Preparation of chiral gamma-substituted-gamma-lactones (1) through kinetic resolution is described. (S)-(-)-1-Phenylethylamine (2) in the presence of anhydrous AlCl(3) shows satisfactory levels of enantioselection in reaction with racemic gamma-substituted-gamma-lactones 1, where (R)-1 remains unreacted, while (S)-1 is enantioselectively converted to the ring-opened amide (S,S)-4. The enantiopurity of (R)-(+)- gamma-substituted gamma-lactones recovered ranges from 62-98% ee.
Patil
Sudhir T
ST
Department of Chemistry, University of Mumbai, Vidyanagari, Kalina, Mumbai, India.
Karnik
Anil V
AV
D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D000643:Ammonium Chloride / Q000494:pharmacology; D002563:Cerium / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D010100:Oxygen / Q000378:metabolism; D010627:Phenethylamines / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D017607:Aluminum Compounds; D002712:Chlorides; D007783:Lactones; D010627:Phenethylamines; D000644:Quaternary Ammonium Compounds; D000643:Ammonium Chloride; C032786:cerium nitrate; D002563:Cerium; D000077410:Aluminum Chloride; D010100:Oxygen