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General experimental procedure: To a cooled solution of dibenzyl azodicarboxylate (DBAD, 328 mg, 1 mmol) and L-proline (11.5 mg, 10 mol , in dry CH3CN (10 mL) at 0°C was added n-butyraldehyde (87 mg, 1.2 mmol, and the mixture was stirred for 2 h at 0°C and further at 10°C for 1 h. This was followed by addition of lithium bromide (130 mg, 1.5 mmol, triethyl phosphonoacetate (336 mg, 1.5 mmol, and DBU (152 mg, 1 mmol) in that sequence, and the whole mixture was stirred at 5°C for 45 min. It was then quenched by the addition of aqueous ammonium chloride solution and extracted with ethyl acetate (3 x 20 mL, The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product 3a, which was then purified by flash column chromatography (packed with silica gel 60-120 mesh) using petroleum ether and ethyl acetate as eluents to afford the pure product
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6: C, 65.44; H, 6.41; N, 6.36. Found: C, 65.25; H, 6.28; N, 6.59%.
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0003870273
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For examples, see: a, Pelletier, S. W, Ed, John Wiley: New York
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For examples, see: (a) Elbein, A.; Molyneux, R. I. In Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley: New York, 1990.
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63
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5. (Chemical Equation Presented)
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5. (Chemical Equation Presented)
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