Iodine-catalyzed aziridination of alkenes using Chloramine-T as a nitrogen source

A structural insight into the P1 S1 binding mode of diaminoethylphosphonic and phosphinic acids, selective inhibitors of alanine aminopeptidases

“…However, obtaining such a material ( 7 ) by nitrene-mediated aziridination appears to be far more problematic. Contrary to the literature data, different versions of both metal and non-metal assisted oxidative additions of Chloramine T ( N -chlorotosylamide sodium salt) to the double bond of 3 are ineffective [17-19]. Extensive optimization of the reaction conditions with other tosyl precursors and hypervalent iodobenzene-based reagents [20-22] finally led to the desired products under copper(I) catalysis [21], but in a very poor yield (< 10% after column chromatography).…”

Nucleophilic Ring‐Opening of N‐o‐Nosylaziridines with N‐Chloro‐N‐Sodiocarbamate: Facile Preparation of Differentially Protected Vicinal Diamines

“…[23] The olefin (6 mmol) was added to a solution of N-chloro-Nsodio-2-nitrobenzesulfonamide (0.78 g, 3 mmol) and iodine (76 mg, 0.3 mmol) in MeCN (10 mL) at room temperature. The solution was stirred in the dark at room temperature for 24 h, quenched with aqueous Na 2 S 2 O 3 (1 m, 5 mL), then extracted with EtOAc (25 mL 4).…”

Recentes avanços na preparação de aziridinas. Aplicações sintéticas e implicações mecanísticas

“…A utilização de iodo molecular ou cloreto de cobre(I) na presença de peneira molecular fornece aziridinas em rendimentos variados 76,77 (16-91%), sendo mais eficiente com olefinas dissubstituídas por grupos alquil ou aril. A metodologia desenvolvida por Sharpless e colaboradores 78 emprega tribrometo de feniltrimetilamônio (PTAB) como catalisador para a aziridinação de olefinas 1,2-dissubstituídas e álcoois alílicos em bons rendimentos, utilizando tanto Cloramina-T anidra quanto tri-hidratada.…”