(2R)-2-hydroxy-2-phenylacetonitrile

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

Procedure: To a solution of L(+)-diisopropyl tartarate (235 mg) in absolute dichloromethane (10 ml), tetaraisopropyl titanate (284 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (436 mg) and then benzaldehyde (424 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol containing the R(+) isomer in the enantiomer excess percentage of 88% was produced in the yield of 37% based on the amount of the used benzaldehyde and 148% based on the amount of the used catalyst. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue stirred at room temperature to obtain a homogeneous solution stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 37%

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

Procedure: To a solution of L(+)-diethyl tartarate (412 mg) in absolute dichloromethane (20 ml), tetaraisopropyl titanate (568 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, to the residue, dichloromethane (20 ml) was added and stirred at room temperature to obtain a homogeneous solution. After cooling the resulting solution to 0° C., hydrogen cyanide (0.4 ml) and then benzaldehyde (212 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol was produced in the yield of 55% which contained the R(+) isomer with the enantiomer excess percentage of 77%. After evaporating volatile components off in the same manner as in Example 1 to the residue, dichloromethane (20 ml) was added stirred at room temperature to obtain a homogeneous solution After cooling the resulting solution to 0° C. stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 55% which

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

Procedure: To a solution of L(+)-tartaric acid derivative shown in Table 1 (2 mmol) in a solvent shown in Table 1 (20 ml), a tetraalkyl titanate shown in Table 1 (2 mmol) was dropwise added and stirred for 30 minutes at room temperature. After evaporating volatile components off in the same manner as in Example 1, a solvent shown in Table 1 (20 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (218 mg) and then benzaldehyde (212 mg) were added and stirred for 14 hours at room temperature. After the reaction, the reaction mixture was treated in the same manner as in Example 1. The product was analyzed by HPLC. The results are shown in Table 1. was dropwise added After evaporating volatile components off in the same manner as in Example 1 was added to the residue stirred at room temperature to obtain a homogeneous solution stirred for 14 hours at room temperature After the reaction the reaction mixture was treated in the same manner as in Example 1

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

Procedure: To a solution of L(+)-diisopropyl tartarate (235 mg) in absolute dichloromethane (10 ml), tetaraisopropyl titanate (284 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (436 mg) and then benzaldehyde (424 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol containing the R(+) isomer in the enantiomer excess percentage of 88% was produced in the yield of 37% based on the amount of the used benzaldehyde and 148% based on the amount of the used catalyst. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue stirred at room temperature to obtain a homogeneous solution stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 37%

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

Procedure: To a solution of L(+)-diethyl tartarate (412 mg) in absolute dichloromethane (20 ml), tetaraisopropyl titanate (568 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, to the residue, dichloromethane (20 ml) was added and stirred at room temperature to obtain a homogeneous solution. After cooling the resulting solution to 0° C., hydrogen cyanide (0.4 ml) and then benzaldehyde (212 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol was produced in the yield of 55% which contained the R(+) isomer with the enantiomer excess percentage of 77%. After evaporating volatile components off in the same manner as in Example 1 to the residue, dichloromethane (20 ml) was added stirred at room temperature to obtain a homogeneous solution After cooling the resulting solution to 0° C. stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 55% which

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

Procedure: To a solution of L(+)-diisopropyl tartarate (235 mg) in absolute dichloromethane (10 ml), tetaraisopropyl titanate (284 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (436 mg) and then benzaldehyde (424 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol containing the R(+) isomer in the enantiomer excess percentage of 88% was produced in the yield of 37% based on the amount of the used benzaldehyde and 148% based on the amount of the used catalyst. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue stirred at room temperature to obtain a homogeneous solution stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 37%

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

Procedure: To a solution of L(+)-tartaric acid derivative shown in Table 1 (2 mmol) in a solvent shown in Table 1 (20 ml), a tetraalkyl titanate shown in Table 1 (2 mmol) was dropwise added and stirred for 30 minutes at room temperature. After evaporating volatile components off in the same manner as in Example 1, a solvent shown in Table 1 (20 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (218 mg) and then benzaldehyde (212 mg) were added and stirred for 14 hours at room temperature. After the reaction, the reaction mixture was treated in the same manner as in Example 1. The product was analyzed by HPLC. The results are shown in Table 1. was dropwise added After evaporating volatile components off in the same manner as in Example 1 was added to the residue stirred at room temperature to obtain a homogeneous solution stirred for 14 hours at room temperature After the reaction the reaction mixture was treated in the same manner as in Example 1

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

Procedure: To a solution of L(+)-diisopropyl tartarate (235 mg) in absolute dichloromethane (10 ml), tetaraisopropyl titanate (284 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (436 mg) and then benzaldehyde (424 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol containing the R(+) isomer in the enantiomer excess percentage of 88% was produced in the yield of 37% based on the amount of the used benzaldehyde and 148% based on the amount of the used catalyst. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue stirred at room temperature to obtain a homogeneous solution stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 37%

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

Procedure: To a solution of L(+)-diethyl tartarate (412 mg) in absolute dichloromethane (20 ml), tetaraisopropyl titanate (568 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, to the residue, dichloromethane (20 ml) was added and stirred at room temperature to obtain a homogeneous solution. After cooling the resulting solution to 0° C., hydrogen cyanide (0.4 ml) and then benzaldehyde (212 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol was produced in the yield of 55% which contained the R(+) isomer with the enantiomer excess percentage of 77%. After evaporating volatile components off in the same manner as in Example 1 to the residue, dichloromethane (20 ml) was added stirred at room temperature to obtain a homogeneous solution After cooling the resulting solution to 0° C. stirred at room temperature for 15 hours Thereafter, the reaction mixture was treated in the same manner as in Example 1 was produced in the yield of 55% which

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

Procedure: To a solution of L(+)-tartaric acid derivative shown in Table 1 (2 mmol) in a solvent shown in Table 1 (20 ml), a tetraalkyl titanate shown in Table 1 (2 mmol) was dropwise added and stirred for 30 minutes at room temperature. After evaporating volatile components off in the same manner as in Example 1, a solvent shown in Table 1 (20 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (218 mg) and then benzaldehyde (212 mg) were added and stirred for 14 hours at room temperature. After the reaction, the reaction mixture was treated in the same manner as in Example 1. The product was analyzed by HPLC. The results are shown in Table 1. was dropwise added After evaporating volatile components off in the same manner as in Example 1 was added to the residue stirred at room temperature to obtain a homogeneous solution stirred for 14 hours at room temperature After the reaction the reaction mixture was treated in the same manner as in Example 1