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 °C in 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.