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,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5-diazabicyclo-[4.3.0]non- 5-ene (DBN) were equally effective in promoting the reaction.
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42
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8644288612
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note
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High diastereselectivity observed is not a result of a thermodynamic equilibration in the presence of a strong base such as TMG, as β-nitroamine 2a with a 55:45 diastereomeric ratio (obtained from a reaction catalyzed by DABCO) was recovered with the same anti/syn ratio after several hours in the presence of 5 mol % TMG.
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44
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8644253073
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note
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2, and toluene, observing a remarkable drop in the rate of the reaction, presumably due to dilution effects.
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45
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8644261942
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note
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Other imines derived from enolizable aliphatic aldehydes were not tested in the reaction due to the lack of methods for the preparation of these compounds.
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8644232970
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note
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In the one-pot protocol, 10 equiv of zinc should be used instead of 9 equiv due to the consumption of the reducing agent for excess 1-nitropropane,
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