Hydrogen Peroxide → (-)-cis-Myrtanol

Participants

Reaction Steps

Hydroborations on a preparative scale were carried out with borane-diisoamyl sulfide and borane-bis(2-methoxyethyl) sulfide for illustrative purposes. Thus (-)-β-pinene (93% ee) was reacted with borane-diisoamyl sulfide and the organoborane intermediate was oxidized with standard 30% hydrogen peroxide and 3M sodium hydroxide used in excess to suppress oxidation of the sulfide. (-)-cis-Myrtanol was isolated by distillation in 82% yield and the sulfide was recovered.

Provenance & Evidence