Hydrogen Peroxide → (-)-cis-Myrtanol

Participants

Reaction Steps

A 6.0M borane adduct (9i) was dissolved in dichloromethane (12 ml) and (-)-β-pinene (5.0 g, 26 mmol), 91% ee was added at 0° C. The reaction was completed in 0.5 h, as indicated in 11B NMR. The mixture was maintained at room temperature for 1 h and oxidized by the addition of 3M sodium hydroxide (5.6 ml, 17 mmol) and 30% hydrogen peroxide (4.0 ml, 40 mmol), keeping the temperature during the addition below 30° C. and then stirring at room temperature overnight. The dichloromethane layer was separated and stirred with water (20 ml) for 0.5 h. The organic layer was separated, dried over anhydrous magnesium sulfate and distilled to give 5.05 g (91%) of pure product, bp 116°-118° C./15 mm Hg. α!20D=-19.4°.

Provenance & Evidence