1-Tetralone → (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

Participants

Reaction Conditions

Reaction Steps

Borane dimethylsulfide complex (2M in THF, 7.0 mL, 0.014 moles) was added over 45 minutes at ambient temperature to a solution of α-tetralone (2.92 g, 0.02 moles) and the title compound of Example 1 (247 mg, 0.001 moles) in THF (80 mL). The reaction mixture was stirred for 15 minutes (at which time thin layer chromatography indicated complete consumption of α-tetralone) and then cooled to 0° C. and quenched with methanol 27 mL). The quenched solution was allowed to warm to ambient temperature, with stirring, for 16 hours. The solvents were removed in vacuo and the residue was redissolved with methylene chloride (50 mL) and pH4 phosphate buffer (50 mL). The phases were separated and the organic phase was washed with water (50 mL), treated with MgSO4 and filtered. The solvent was removed in vacuo to afford 2.93 (99%) of -(R)-(+)-1,2,3,4-tetrahydro-1-naphthol as a white solid. HPLC with a chiral support demonstrated that the product had a 94% e.e.

Provenance & Evidence