Asymmetric synthesis of the epimeric (3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanones.
The asymmetric rhodium-catalysed 1,4-addition of alkenylzirconium reagents to 2-cyclohexenone can be useful in the synthesis of 3-alkenyl-2-methylcyclohexanones, provided that formaldehyde is used in trapping the intermediate zirconium enolates. In this manner a four-step sequence leading to the two epimeric 3-hexenyl-2-methylcyclohexanones in enantiomeric form was developed.
Vrielynck
Freek A
FA
Ghent University, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan 281 (S4), B-9000 Gent, Belgium.
De Clercq
Pierre J
PJ
D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D012238:Rhodium / Q000494:pharmacology*; D013237:Stereoisomerism
C523693:3-(hex-1-enyl)-2-methylcyclohexanone; D003510:Cyclohexanes; D003512:Cyclohexanones; C506365:Cyclohexane; D012238:Rhodium