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

Participants

Reaction Steps

To 100 mL of an autoclave was charged 11.7 mg (0.010 mmol) of the mixture of RuCl2[(R)-binap](dmf)n and RuCl2[(S) -binap][(S)-binaphthyldiamine]. 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 228 mg (yield: 53%) of (R)-1-(1-naphthyl)ethanol was obtained. The enantio-selectivity was 4%ee.

Provenance & Evidence