Simple and practical routes to enantiomerically pure 5-(trialkylsilyl)-2-cyclohexenones.
[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.
Sarakinos
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Department of Chemistry and Chemical Biology, 12 Oxford Street, Harvard University, Cambridge, Massachusetts 02138, USA.
Corey
E J
EJ
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
D003512:Cyclohexanones; D017646:Organosilicon Compounds