Reaction SMILES: [CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].O.C(C(C(C(OCC)=O)O)O)(OCC)=[O:27].C(N(C(C)C)CC)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([CH2:14][S@:15]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:27])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]
Reactant: Cc1c(OCC(F)(F)F)ccnc1CSc1nc2ccccc2[nH]1
Reactant: CCOC(=O)C(O)C(O)C(=O)OCC
Agent: [Ti+4]
Agent: CC(C)[O-]
Agent: O=S([O-])([O-])=S
Solvent: Cc1ccccc1
Solvent: CCN(C(C)C)C(C)C
Solvent: O
Product: Cc1c(OCC(F)(F)F)ccnc1C[S@@](=O)c1nc2ccccc2[nH]1
Reaction time: 0.5 h
Yield: 164.4 %

Procedure:
In a stream of nitrogen, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]thio]benzimidazole (4.5 kg, 12.7 mol, water content of 1.89 g), toluene (22 L), water (25 g, 1.39 mol, total water content of 1.49 mol) and (+)-diethyl tartrate (0.958 L, 5.60 mol) were mixed. In a stream of nitrogen, to the mixture was added titanium(IV) isopropoxide (0.747 L, 2.53 mol) at 50 to 60° C., and stirred for 30 minutes at the same temperature. In a stream of nitrogen, to the resulting mixture liquid was added diisopropylethylamine (0.733 L, 4.44 mol) at a room temperature, further added cumenehydroperoxide (6.88 L, content of 82%, 37.5 mol) at −5 to 5° C., and stirred at −5 to 5° C. for 1.5 hours to obtain a liquid reaction mixture. In a stream of nitrogen, to the reaction liquid was added 30% sodium thiosulfate aqueous solution (17 L) to decompose residual cumenehydroperoxide. The reaction liquid was phase-separated, and water (4.5 L), heptane (13.5 L), t-butyl methyl ether (18 L) and heptane (27 L) were successively added to the resulting organic phase, and the mixture was subjected to crystallization under stirring. The resulting crystal was separated and washed with t-butyl methyl ether-toluene (t-butyl methyl ether:toluene=4:1) (4 L). Under stirring, an acetone (20 L) suspension of the wet crystal was added dropwise to a liquid mixture of acetone (7 L) and water (34 L), and then added water (47 L) thereto. The precipitated crystal was separated and washed with acetone-water (acetone:water=1:3) (4 L) and with water (12 L). The wet crystal was dissolved in ethyl acetate (45 L) and water (3 L) to be phase-separated. A slight amount of insoluble matter (undissolved material) in an organic phase was filtrated off, and then triethylamine (0.2 L) was added to the organic phase and concentrated under a reduced pressure until the liquid volume of the organic phase was to about 7 L. To the resultant condensate were added methanol (2.3 L), about 12.5% aqueous ammonia (23 L) at about 50° C. and t-butyl methyl ether (22 L) at about 50° C. to be phase-separated. To the resultant organic phase was added about 12.5% aqueous ammonia (11 L) to be phase-separated (the operation was repeated once). The aqueous phases were combined with each other, ethyl acetate (22 L) was added thereto, and under cooling, acetic acid was added dropwise thereto for adjusting pH to about 8. The resulting liquid was phase-separated and the resultant aqueous phase was extracted with ethyl acetate (11 L). The organic phases were combined with each other, and washed with about 20% brine (11 L). After adding triethylamine (0.2 L), the organic phase was concentrated under a reduced pressure. To the concentrate was added acetone (5 L) and concentrated under a reduced pressure. The resulting concentrate was dissolved in acetone (9 L), the resulting mixture was added dropwise to a mixture liquid of acetone (4.5 L) and water (22.5 L), and then water (18 L) was added dropwise thereto. The precipitated crystal was separated, and was washed with cold acetone-water (acetone:water=1:3) (3 L) and water (12 L), successively. The wet crystal was dissolved in ethyl acetate (32 L). The separated aqueous phase was separated by separation operation, and the resulting organic phase was concentrated under a reduced pressure until the liquid volume became to be about 14 L. To the residue were added ethyl acetate (36 L) and active carbon (270 g), and after stirring, active carbon was filtered off. The resultant filtrate was concentrated under a reduced pressure until the liquid volume was to about 14 L. To the concetrate was added dropwise heptane (90 L) at about 40° C. After stirring at the same temperature for about 30 minutes, the resultant crystal was separated, and washed with ethyl acetate-heptane (ethyl acetate:heptane=1:8, 6L) at about 40° C. After drying, the title compound (3.4 kg) was obtained. The enantiomer excess rate of the compound was 100%ee.