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

Freek A Vrielynck; Pierre J De Clercq

doi:10.3390/12020237

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

Molecules. 2007 Feb 21;12(2):237-44. doi: 10.3390/12020237.

Authors

Freek A Vrielynck¹, Pierre J De Clercq

Affiliation

¹ 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclohexanes / chemical synthesis*
Cyclohexanes / chemistry
Cyclohexanones / chemical synthesis*
Cyclohexanones / chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Rhodium / pharmacology*
Stereoisomerism

Substances

3-(hex-1-enyl)-2-methylcyclohexanone
Cyclohexanes
Cyclohexanones
Cyclohexane
Rhodium