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

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

Procedure: Washed phaseolus aureus L (green grams) 50 g. were taken into a conical flask and allowed to soak in deionised water (400 ml) for a period of 24 hr. 1-naphthalenone (0.500 g; 0.0034 moles) III was added to the soaked phaseolus aureus L (green grams) in the above water, covered and allowed to shake for 46 hr at 15–20° C. Then the green grams were filtered off and washed with deionised water (3×100 ml). The combined filtrate was extracted with chloroform (3×500 ml). The chloroform layer was dried and the crude product obtained (480 mg). Pure (1S)-1,2,3,4-tetrahydro-1-naphthalenol (IV) was obtained after column chromatography with silica gel using chloroform as eluent. Washed phaseolus aureus L (green grams) 50 g were taken into a conical flask to shake for 46 hr at 15–20° C Then the green grams were filtered off washed with deionised water (3×100 ml) The combined filtrate was extracted with chloroform (3×500 ml) The chloroform layer was dried the crude product obtained (480 mg)

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

Procedure: Washed phaseolus aureus L (green grams) 50 g. were taken into a conical flask and allowed to soak in deionised water (400 ml) for a period of 24 hr. 1-naphthalenone (0.500 g; 0.0034 moles) III was added to the soaked phaseolus aureus L (green grams) in the above water, covered and allowed to shake for 46 hr at 15–20° C. Then the green grams were filtered off and washed with deionised water (3×100 ml). The combined filtrate was extracted with chloroform (3×500 ml). The chloroform layer was dried and the crude product obtained (480 mg). Pure (1S)-1,2,3,4-tetrahydro-1-naphthalenol (IV) was obtained after column chromatography with silica gel using chloroform as eluent. Washed phaseolus aureus L (green grams) 50 g were taken into a conical flask to shake for 46 hr at 15–20° C Then the green grams were filtered off washed with deionised water (3×100 ml) The combined filtrate was extracted with chloroform (3×500 ml) The chloroform layer was dried the crude product obtained (480 mg)

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

Procedure: (R)-2-amino-2-cyclohexyl-1,1-diphenylethanol (59 mg, 0.2 mmol), dry tetrahydrofuran (2 mL) and trimethylborate (27.2 μL, 0.24 mmol) were added to a dry flask and stirred under an atmosphere of nitrogen for 1.5 hours to form a solution of (R)-4-cyclohexyl-5,5-diphenyl-2-methoxy-1,3,2-oxazaborolidine. To this solution was added borane dimethylsulfide complex (100 μL, 1.0 mmol) and the mixture was stirred at room temperature for a further 30 minutes. A solution of 1-tetralone (133 μL, 1.0 mmol) in tetrahydrofuran (5 mL) was added by means of a syringe pump at a rate of 16 mL/min and the reaction was then stirred for a further 1 hour. Thin layer chromatography (silica gel/hexane/ethyl acetate 4:1) showed no starting material. The reaction was quenched by addition of methanol. The solvent was evaporated under vacuum and the residue was dissolved in ethyl acetate and washed 3 times with IN HCl. The ethyl acetate solution was dried over magnesium sulfate, filtered through a plug of silica gel and concentrated to give (S)-1-hydroxy-1,2,3,4-tetrahydronaphthalene with an ee of 96.5%. The enantiomer ratio was determined by HPLC using a Chiralcel OB 25 cm×4.6 mm column with hexane/2-propanol (9:1) mobile phase at 0.5 mL/min at 25° C. Detection with UV was at 254 nm. To this solution was added borane dimethylsulfide complex (100 μL, 1.0 mmol) the reaction was then stirred for a further 1 hour The reaction was quenched by addition of methanol The solvent was evaporated under vacuum the residue was dissolved in ethyl acetate washed 3 times with IN HCl The ethyl acetate solution was dried over magnesium sulfate filtered through a plug of silica gel concentrated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL autoclave with a stirrer, trans-RuCl2[(R)-dm-segphos][(S)-daiPen] (3.6 mg, 0.003 mol, 1/1,000 molar fold of 1-tetralone) was added. After purging with nitrogen, 2-propanol (3 mL), 1-tetralone (439 mg, 3 mmol) and 2-propanol solution of t-BuOK (0.1 mol/L, 0.3 mL, 0.03 mmol) were added. Subsequently, purging with hydrogen, the mixture was stirred at 25° C. for 15 hours under hydrogen pressure of 1 MPa. As a result of analysis of the reaction solution by using gas chromatography (Chirasil-DEX CB), it was found that the conversion rate is 42% and the optical purity is 90% ee. were added Subsequently, purging with hydrogen As a result of analysis of the reaction solution

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL autoclave with a stirrer, RuCl[(R)-dm-segphos][(S)-daipen] obtained from Example 5 above (3.5 mg, 0.003 mol, 1/1,000 molar fold of 1-tetralone) were added. After purging with nitrogen, 2-propanol (3 mL), 1-tetralone (439 mg, 3 mmol) and 2-propanol solution of t-BuOK (0.1 mol/L, 0.3 mL, 0.03 mmol) were added. Subsequently, purging with hydrogen, the mixture was stirred at 25° C. for 15 hours under hydrogen pressure of 1 MPa. As a result of analysis of the reaction solution by using gas chromatography (Chirasil-DEX CB), it was found that the conversion rate is 99% or more and the optical purity is 96% ex. were added Subsequently, purging with hydrogen As a result of analysis of the reaction solution

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

Procedure: Washed phaseolus aureus L (green grams) 50 g. were taken into a conical flask and allowed to soak in deionised water (400 ml) for a period of 24 hr. 1-naphthalenone (0.500 g; 0.0034 moles) III was added to the soaked phaseolus aureus L (green grams) in the above water, covered and allowed to shake for 46 hr at 15–20° C. Then the green grams were filtered off and washed with deionised water (3×100 ml). The combined filtrate was extracted with chloroform (3×500 ml). The chloroform layer was dried and the crude product obtained (480 mg). Pure (1S)-1,2,3,4-tetrahydro-1-naphthalenol (IV) was obtained after column chromatography with silica gel using chloroform as eluent. Washed phaseolus aureus L (green grams) 50 g were taken into a conical flask to shake for 46 hr at 15–20° C Then the green grams were filtered off washed with deionised water (3×100 ml) The combined filtrate was extracted with chloroform (3×500 ml) The chloroform layer was dried the crude product obtained (480 mg)