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

doi:10.3390/12020237

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

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

Freek A. Vrielynck and Pierre J. De Clercq *

Ghent University, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan 281 (S4), B-9000 Gent, Belgium

^* Author to whom correspondence should be addressed.

Received: 9 January 2007; in revised form: 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.

Keywords: Enantioselective 1; 4-addition;zirconium O-enolate trapping;2-cyclo-hexenone.

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MDPI and ACS Style

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.

AMA Style

Vrielynck F.A., De Clercq P.J. Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones. Molecules. 2007; 12(2):237-244.

Chicago/Turabian Style

Vrielynck, Freek A.; De Clercq, Pierre J. 2007. "Asymmetric Synthesis of the Epimeric (3S)-3-((E)-Hex-1-enyl)-2-methylcyclohexanones." Molecules 12, no. 2: 237-244.

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