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9644305561
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note
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The direct conversion of 5 to 4 via the corresponding dialdehyde resulted in a low yield of 4
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33
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9644298691
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note
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3, Z = 4, R = 0.037, Rw = 0.021
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34
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9644286874
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note
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3
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9644309938
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note
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4 and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1:8) to afford the product in 62% yield with 84% ee. The enantiomeric excess of the products was determined by HPLC analysis using a chiral stationary phase column (Daicel Chiralpak AS, hexane/i-PrOH = 9:1, flow rate = 0.5 mL/min)
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39
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0142040727
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2O (0.05 mmol) in EtOH (1.5 mL) was stirred at rt for 1 h. To the resulting clear blue solution was added nitromethane (10 mmol) and p-nitrobenzaldehyde (1.0 mmol). After stirring for a further 24 h at rt, the volatile components were removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1:8) to afford the product in 98% yield with 65% ee. The enantiomeric excess of the products was determined by HPLC analysis using a chiral stationary phase column (Daicel Chiralcel OD-H, hexane/i-PrOH = 9:1, flow rate = 1.0 mL/min). The product was identical in all respects to the spectra reported by Evans et al., D.A. Evans, D. Seidel, M. Rueping, H.W. Lam, J.T. Shaw, and C.W. Downey J. Am. Chem. Soc. 125 2003 12692
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Evans, D.A.1
Seidel, D.2
Rueping, M.3
Lam, H.W.4
Shaw, J.T.5
Downey, C.W.6
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