[CH3:1][CH2:2][C@H:3]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.CS(N)(=O)=O.[C:64]1([C:70]2[N:71]=C(C3CCCCC=3)[O:73][C:74]=2[C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.S([O-])([O-])=[O:88].[Na+].[Na+].[CH3:93][C:94]([OH:97])([CH3:96])[CH3:95]>O>[OH:97][C@:94]1([C:96]2[O:73][C:74]([C:75]3[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=3)=[C:70]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[N:71]=2)[CH2:95][CH2:3][CH2:2][CH2:1][C@@H:93]1[OH:88]A solution of AD-mix-α® (30 g) in a mixture of t-BuOH (600 ml) and water (600 ml) was stirred for 1 hour, and then methanesulfonamide (9.3 g) and 1-(4,5-diphenyloxazol-2-yl)-1-cyclohexene added to the solution at room temperature. After being stirred for 20 hours at the same temperature, sodium sulfite (60 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane (30 g).
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