1-Acetylnaphthalene → (1R)-1-(Naphthalen-1-yl)ethan-1-ol

Participants

Reaction Steps

A 100 mL autoclave was charged with 11.7 mg (0.010 mmol) of the mixture of RuCl2[(S)-dm-binap][(S,S)-dpen] and RuCl2[(R)-dm-binap][(R)-3,3′-dimethyl-1,1′-binaphthyl-2,2′-diamine] obtained in Example 2. After purging with argon, 2.8 mL of 2-propanol and 50 μL (0.025 mmol) of KOH/2-propanol (0.5M solution) were added. The resulting mixture was stirred at room temperature for 30 minutes. After addition of 0.38 mL (2.5 mmol) of 1′-acetonaphthone, stirring was conducted at room temperature for 4 hours at a hydrogen pressure adjusted to 0.8 Mpa. The reaction mixture was concentrated by distilling off the solvent under reduced pressure. The residue was filtered using silica gel, whereby 420 mg (yield: 98.7%) of (R)-1-(1-naphthyl)ethanol was obtained. The enantio-selectivity was 96.2%ee.

Provenance & Evidence