title: Simple and practical routes to enantiomerically pure 5-(trialkylsilyl)-2-cyclohexenones.
abstract: [reaction: see text] Enantiomerically pure chiral 5-silylated 2-cyclohexenones are easily prepared in high yield using as a key step kinetic resolution with a commercially available lipase. Fully active enzyme can be recovered very efficiently for reuse. The synthetic steps are outlined in Schemes 1 and 3. Enantiomerically pure 2-cyclohexenones such as 1 and 2 are versatile intermediates for the synthesis of a multitude of chiral targets by means of a variety of diastereoselective reactions such as those illustrated in Scheme 2.
authors.affiliation: Department of Chemistry and Chemical Biology, 12 Oxford Street, Harvard University, Cambridge, Massachusetts 02138, USA.
authors.forename: G
authors.initials: G
authors.lastname: Sarakinos
authors.forename: E J
authors.initials: EJ
authors.lastname: Corey
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D017646:Organosilicon Compounds / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D003512:Cyclohexanones; D017646:Organosilicon Compounds