Synthesis of 1,2,5- and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization

Late Transition Metal-Catalyzed Hydroamination and Hydroamidation

“…In the presence of 2 mol % CuCl 2 , γ- N -Boc- or N -tosyl-4-amino-1-yn-3-ols undergo intramolecular hydroamidation followed by dehydration to form pyrroles (Scheme ). , Ag and Pd complexes were also reported to be efficient catalysts for this elegant pyrrole synthesis. , …”

Silver-catalysed reactions of alkynes: recent advances

“…Lee and Ha et al described the ring-opening/recyclization reaction of 1-(aziridin-2yl)propargylic alcohols 166 (Scheme 64). 139 In the presence of nucleophiles such as HOAc and TMSN 3 , intermediates 166-1 and 166-2 could be generated under mild conditions, and Ag(I)-catalysed intramolecular hydroamination subsequently occurred, resulting in the formation of 1,2,5-tri-and 1,2,3,5-tetra-substituted pyrroles 167 and 168 in good yields.…”

Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols

“…The second step, leading to the aziridine, comprises the treatment of 2,3-dibromopropanoate with benzylamine and (S)-α-methylbenzylamine, respectively. [8] (1'S,2S)-2b R = Me (96%) [9] (1'S,2R)-2b R = Me (86%) 3a R = H, R' = Me (44%) [10] (1'S,2S)-3c R = R' = Me (28%) [1d] (1'S,2S)-3d R = Me, R' = Ph (33%) [1d] 3b R = H, R' = Ph (55%) [8,11] (1'S,2R)-3e R = Me, R' = Ph (42%) [12] R R 85% Me(MeO)NH HCl .…”