(1R)-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetralone (200 ml, 1.5 mol) was charged to the catalyst solution, followed by 2-propanol (0.5 l). The pressure was reduced (28.5 mmHg) and then a sodium 2-propoxide solution (120 ml of 0.1M solution in 2-propanol) was charged. The mixture was stirred at ambient temperature under nitrogen for 4.5 h, at hourly intervals the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 96.9%, ee 86.9%. The turnover number, integrated over 1 h, was 358 h−1. charged removed by distillation

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium 2-propoxide (0.38 ml of 0.1M solution in 2-propanol) was charged to the catalyst solution followed by the α-tetralone (0.5 ml, 3.76 mmol). The mixture was stirred under vacuum (80 mmHg) at 35° C. for 2 h, after the first hour the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 98.4%, ee 95.7%. The turnover number, integrated over 1 h, was 185 h−1. charged removed by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using substantially the same procedure as recited in Example 4 but substituting the title compound of Example 2 for the title compound of Example 1, the title compound of Example 12 was prepared in 88% e.e.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using substantially the same procedure as recited in Example 4 but substituting the title compound of Example 2 for the title compound of Example 1, the title compound of Example 12 was prepared in 88% e.e.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. (at which time thin layer chromatography indicated complete consumption of α-tetralone) quenched with methanol 27 mL) to warm to ambient temperature with stirring, for 16 hours The solvents were removed in vacuo the residue was redissolved with methylene chloride (50 mL) and pH4 phosphate buffer (50 mL) The phases were separated the organic phase was washed with water (50 mL) treated with MgSO4 filtered The solvent was removed in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: General procedure for hydrogenation: Hydrogenation of 28 illustrates the typical reaction procedure: To a mixture of 1-tetralone, 28, (10.0 g, 66.4 mmol) and RuCl2[(2R,2′R,3S,3′S)-MeO-BIBOP](amqui), 27, (1.0 mg, 0.001 mmol, 0.002 mol %) was added isopropanol (40 mL) and a 1 M solution of t-BuOK in tert-butanol (1.33 mL, 1.33 mmol, 0.02 equiv). The autoclave reactor was first purged with nitrogen, then with hydrogen, and then the reaction mixture was stirred at 60° C. under 400 psi of hydrogen for 20 h. After venting the hydrogen gas, the solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography with ethyl acetate/hexane (0-50%) as eluent to give (R)-1,2,3,4-tetrahydro-1-naphthol, 29, (colorless oil, 9.6 g, 98% yield, 96:4 er). The er of 1,2,3,4-tetrahydro-1-naphthol was determined by HPLC analysis: column, Chiralcel OJ-3, 4.6×150 mm; eluent, heptane/isopropanol (95:5); flow rate, 1 mL/min; column temperature, 25° C.; retention time (tR) of (R)-1,2,3,4-tetrahydro-1-naphthol, 7.45 min (95.8%); tR of (S)-1,2,3,4-tetrahydro-1-naphthol, 5.75 min (4.2%). [α]D=−31.2 (c=2.0, MeOH). the typical reaction procedure The autoclave reactor was first purged with nitrogen the solvent was removed under reduced pressure The residue was purified by silica-gel column chromatography with ethyl acetate/hexane (0-50%) as eluent

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: General procedure for hydrogenation: Hydrogenation of 28 illustrates the typical reaction procedure: To a mixture of 1-tetralone, 28, (10.0 g, 66.4 mmol) and RuCl2[(2R,2′R,3S,3′S)-MeO-BIBOP](amqui), 27, (1.0 mg, 0.001 mmol, 0.002 mol %) was added isopropanol (40 mL) and a 1 M solution of t-BuOK in tert-butanol (1.33 mL, 1.33 mmol, 0.02 equiv). The autoclave reactor was first purged with nitrogen, then with hydrogen, and then the reaction mixture was stirred at 60° C. under 400 psi of hydrogen for 20 h. After venting the hydrogen gas, the solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography with ethyl acetate/hexane (0-50%) as eluent to give (R)-1,2,3,4-tetrahydro-1-naphthol, 29, (colorless oil, 9.6 g, 98% yield, 96:4 er). The er of 1,2,3,4-tetrahydro-1-naphthol was determined by HPLC analysis: column, Chiralcel OJ-3, 4.6×150 mm; eluent, heptane/isopropanol (95:5); flow rate, 1 mL/min; column temperature, 25° C.; retention time (tR) of (R)-1,2,3,4-tetrahydro-1-naphthol, 7.45 min (95.8%); tR of (S)-1,2,3,4-tetrahydro-1-naphthol, 5.75 min (4.2%). [α]D=−31.2 (c=2.0, MeOH). the typical reaction procedure The autoclave reactor was first purged with nitrogen the solvent was removed under reduced pressure The residue was purified by silica-gel column chromatography with ethyl acetate/hexane (0-50%) as eluent

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50-ml autoclave, 3.3 mg (0.005 mmol, S/C=1000) of RuCl((R,R)—O-HT-Tsdpen) was placed, and the autoclave was purged with nitrogen. Subsequently, 0.73 g (5.0 mmol) of α-tetralone and 4.4 ml of methanol were added thereto, then hydrogen gas was charged to 3.0 MPa. Subsequently, the mixture was stirred for 20 hours at 60° C. The reaction liquid was subjected to a GC analysis, and as a result, (R)-1-tetralol was obtained at a conversion rate of 52.0% with an optical purity of 99.3% ee. the autoclave was purged with nitrogen The reaction liquid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetralone (200 ml, 1.5 mol) was charged to the catalyst solution, followed by 2-propanol (0.5 l). The pressure was reduced (28.5 mmHg) and then a sodium 2-propoxide solution (120ml of 0.1M solution in 2-propanol) was charged. The mixture was stirred at ambient temperature under nitrogen for 4.5 h, at hourly intervals the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 96.9%, ee 86.9%. The turnover number, integrated over 1 h, was 358 h−1. charged removed by distillation

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium 2-propoxide (0.38 ml of 0.1M solution in 2-propanol) was charged to the catalyst solution followed by the α-tetralone (0.5 ml, 3.76 mmol). The mixture was stirred under vacuum (80 mmHg) at 35° C. for 2 h, after the first hour the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 98.4%, ee 95.7%. The turnover number, integrated over 1 h, was 185 h−1 charged removed by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetralone (200 ml, 1.5 mol) was charged to the catalyst solution, followed by 2-propanol (0.5 l). The pressure was reduced (28.5 mmHg) and then a sodium 2-propoxide solution (120 ml of 0.1M solution in 2-propanol) was charged. The mixture was stirred at ambient temperature under nitrogen for 4.5 h, at hourly intervals the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 96.9%, ee 86.9%. The turnover number, integrated over 1 h, was 358 h−1. charged removed by distillation

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium 2-propoxide (0.38 ml of 0.1M solution in 2-propanol) was charged to the catalyst solution followed by the α-tetralone (0.5 ml, 3.76 mmol). The mixture was stirred under vacuum (80 mmHg) at 35° C. for 2 h, after the first hour the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-tetralol Yield 98.4%, ee 95.7%. The turnover number, integrated over 1 h, was 185 h−1. charged removed by distillation