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...

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Published inMolecules (Basel, Switzerland) Vol. 12; no. 2; pp. 237 - 244
Main Authors Vrielynck, Freek A, De Clercq, Pierre J
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 21.02.2007
MDPI
Subjects
2-cyclo-hexenone
4-addition
Alcohol
Catalysis
Cyclohexanes - chemical synthesis
Cyclohexanes - chemistry
Cyclohexanones - chemical synthesis
Cyclohexanones - chemistry
Enantioselective 1
Ligands
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Reagents
Rhodium - pharmacology
Stereoisomerism
Zirconium
zirconium O-enolate trapping
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Summary: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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/12020237