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85039659985
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note
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Typical experimental procedure is exemplified by the aziridination of styrene: under nitrogen atmosphere, a toluene solution (0.25 mL) of complex 1 (1.9 mg, 2 μmol) was concentrated twice azeotropically in vacuo. MS 4A (20 mg) and styrene (10.4 mg, 0.1 mmol) were added to the residue. To the mixture was added dichloromethane (0.5 mL) and the resulting suspension was stirred for 0.5 h at room temperature. To the suspension was added p-toluenesulfonyl azide (15.5 μL, 0.1 mmol) and stirred for 24 h. The reaction mixture was directly chromatographed on silica gel using hexane and ethyl acetate (hexane:ethyl acetate = 1/0-19/1-8/2) to give the corresponding aziridine (19.4 mg) in 71% yield. The enantiomeric excess of the product was determined by HPLC analysis using DAICEL CHIRALCEL OJ-H (hexane:i-PrOH = 1:1).
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26
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33751499952
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It has been reported that metal nitrenoid species undergoes aziridination and allylic C-H amination competitively: D. Evans, M. M. Faul, and M. T. Bilodeeau, J. Org. Chem., 56, 6744 (1991).
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Evans, D.1
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27
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0343597826
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A similar approaching model has been proposed for Mn(salen)-catalyzed epoxidation via the corresponding oxo manganese species: B. D. Brandes and E. N. Jacobsen, J. Org. Chem., 59, 4378 (1994).
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Brandes, B.D.1
Jacobsen, E.N.2
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