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Molecules 2007, 12(2), 237-244; https://doi.org/10.3390/12020237

Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones

Ghent University, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan 281 (S4), B-9000 Gent, Belgium
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Received: 9 January 2007 / Revised: 20 February 2007 / Accepted: 20 February 2007 / Published: 21 February 2007
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Abstract

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. View Full-Text
Keywords: Enantioselective 1; 4-addition;zirconium O-enolate trapping;2-cyclo-hexenone. Enantioselective 1; 4-addition;zirconium O-enolate trapping;2-cyclo-hexenone.
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Vrielynck, F.A.; De Clercq, P.J. Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones. Molecules 2007, 12, 237-244.

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