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Chiral N-protected amino allenes have been synthesized from 3-alkyl-2-ethynylaziridines via organocopper-mediated reactions. Treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-2-ethynylaziridines with RCu(CN)M (M=Li or MgX) in THF at -78 o C affords exclusively the expected (S,S)-amino allenes in high yields in a regio- and stereoselective manner. On the other hand, (2S,3S)-2,3-cis-3-alkyl-2-ethynylaziridines...
Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding 2,3-trans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols to Pd(PPh 3 ) 4 (5–20 mol%) in THF or 1,4-dioxane affords predominantly the corresponding 2,3-cis-2-alkenyl-3-alkylaziridines...
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