The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide.
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols10-12,sulfonylbicyclo[5.2.0]-nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 degrees C in THF reacts with (+/-)-phenyl vinyl sulfoxide and upon oxidation with MCPBA, the cyclohexanone 4 and monoalkylated cyclobutanone 5 were obtained. The ratio of bicyclo[n.2.0]alkan-1-ol to alkylated products varied with the ketone enolate, conversion of phenyl vinyl sulfoxide, time, temperature and concentration of reaction and the stability and steric strain of the final bicyclo[n.2.0]alkan-1-ol product.
Loughlin
Wendy A
WA
School of Science, Griffith University, Brisbane, QLD, 4111, Australia. w.loughlin@sct.gu.edu.au
McCleary
Michelle A
MA