Water → (1R,2S)-1,2-Cyclooctanediol

Participants

Reaction Conditions

Reaction Steps

Cyclooctene (4.41 g) was dissolved in acetonitrile (45 mL) and water (15 mL), and to the solution were added N-methylmorpholine N-oxide (5.15 g), microencapsulated osmium tetraoxide (1 g, 10% osmium tetraoxide content), followed by stirring at 40-50° C. for 21 hours. Any insoluble microencapsulated osmium was filtered off, and was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1), to thereby give the title compound (4.97 g).

Provenance & Evidence