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61349157126
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Typical experimental procedure (Table 2, entry 3, Nb-imidazoline (7.3 mg, 8.25μmol) and CuCl (0.74 mg, 7.5 μmol) were stirred for 3 h at rt in CH2Cl2(1.5 mL) under Ar atmosphere. To the solution were added 1,2-butanediol (11 μL, 0.15 mmol, i-Pr2NEt (25.7 μL, 0.15 mmol, and o-methylbenzoyl chloride (9.7 μL, 0.075 mmol) at -40 °C. After stirring for 20 h, the solution was poured onto water and the aqueous layer was extracted with CHCl3 (10 mL x 3, The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo after filtration. The residual crude product was purified by silica gel chromatography (hexane:EtOAc, 3:1) to give the product. The ee of the adduct was determined by chiral stationary phase HPLC analysis Daicel Chiralpak AS-H
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4 and concentrated in vacuo after filtration. The residual crude product was purified by silica gel chromatography (hexane:EtOAc = 3:1) to give the product. The ee of the adduct was determined by chiral stationary phase HPLC analysis (Daicel Chiralpak AS-H).
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25
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61349183581
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In the reaction using pheny-1,2-ethanediol, when the major secondary alcohol 1 was obtained in 36% yield with 54% ee and the minor primary alcohol 2 was obtained in 7% yield with 73% ee, the (S)-enriched starting diol was recovered in 41% with 29% ee
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In the reaction using pheny-1,2-ethanediol, when the major secondary alcohol 1 was obtained in 36% yield with 54% ee and the minor primary alcohol 2 was obtained in 7% yield with 73% ee, the (S)-enriched starting diol was recovered in 41% with 29% ee.
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0142040727
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Downey, C.W.6
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