(1R)-1-(2-methylphenyl)ethanol

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

Procedure: (S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e. worked-up to yield a liquid with a white precipitate the suspension was filtered to remove the precipitate the resulting filtrate was concentrated

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

Procedure: (S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e. worked-up to yield a liquid with a white precipitate the suspension was filtered to remove the precipitate the resulting filtrate was concentrated

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

Procedure: 2′-methylacetophenone and (S)-(−)-2-methyl-CBS-oxazaborolidine were reacted as described in Example 35, Step 1 to provide (R)-1-o-Tolyl-ethanol.

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

Procedure: (S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e. worked-up to yield a liquid with a white precipitate the suspension was filtered to remove the precipitate the resulting filtrate was concentrated

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

Procedure: (S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e. worked-up to yield a liquid with a white precipitate the suspension was filtered to remove the precipitate the resulting filtrate was concentrated

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

Procedure: 2′-methylacetophenone and (S)-(−)-2-methyl-CBS-oxazaborolidine were reacted as described in Example 35, Step 1 to provide (R)-1-o-Tolyl-ethanol.

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

Procedure: (S)-(−)-2-Methyl-CBS-oxazaborolidine (3.72 g, 13.4 mmol) was dissolved in THF (60 mL). Borane methyl sulfide complex (2M in THF; 36.6 mL, 73.3 mmol) was added, and the mixture was cooled to 0° C. 2′-Methylacetophenone (15 g, 111 mmol) in THF (30 mL) was added over 1 hour, and the mixture was then worked-up to yield a liquid with a white precipitate. Hexanes was added, the suspension was filtered to remove the precipitate, and the resulting filtrate was concentrated to give the title compound in 93% e.e. worked-up to yield a liquid with a white precipitate the suspension was filtered to remove the precipitate the resulting filtrate was concentrated

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

Procedure: 2′-methylacetophenone and (S)-(−)-2-methyl-CBS-oxazaborolidine were reacted as described in Example 35, Step 1 to provide (R)-1-o-Tolyl-ethanol.