Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- (or) 3-substituted indoles to non-activated aziridine 2-carboxaldehydes in dioxane afforded 2-(indol-3-ylhydroxymethyl)aziridines whose ring openings with various nucleophiles rendered multi-substituted tryptamine derivatives....

Chiral contiguous bisaziridines were prepared by the aziridination of chiral 3‐[1‐(1‐phenylethyl)aziridin‐2‐yl)]acrylaldehydes with either N‐Boc‐O‐tosyl or N‐Ts‐O‐tosyl hydroxylamine as a nitrogen source and (2R)‐ or (2S)‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as a chiral organocatalyst. The regioselective ring opening of bisaziridines afforded chiral nitrogen‐rich molecules.