Investigations into the reaction of the lithium enolate of cyclohexanone and phenyl vinyl sulfoxide: A simple synthesis of a bicyclo[4.2.0]octan-1-ol

Abstract

The enolate generated from cyclohexanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide to give the novel sulfinylbicyclo[4.2.0]octanols 1-3 and monoalkylated sulfoxide 4. The effects of changes in temperature, concentration, and reaction time were studied. By accurate control of temperature, concentration, and reaction time the ratio of bicyclooctanols 1-3 to monoalkylated sulfoxide 4 obtained was 95 5. The bicyclooctanols 1-3 were characterised as the sulfones 5 and 6. The relative stereochemistries of the bicyclooctanols 1-3 were established by X-ray structural determination.