Molecules. 2007 Feb 21;12(2):237-44.

Asymmetric synthesis of the epimeric (3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanones.

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

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.

PMID:: 17846574; [PubMed - indexed for MEDLINE]

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Asymmetric synthesis of the epimeric (3S)-3-((E)-hex-1-enyl)-2-methylcyclohexanones.

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