Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

Aziridine Ring Opening: An Overview of Sustainable Methods

“…Since they are non‐flammable, non‐volatile and recyclable, they could be effectively used as green solvents . Aggarwal and co‐workers reported a novel methodology for the ring opening of NH‐aziridines 56 by various aromatic and aliphatic thiols in the presence of ionic liquids at room temperature (Scheme ) . They reported that 1‐butyl‐3‐methylimidazolium (BMIM) chloride gave the ring‐opened product 57 in better yields than BMIM bromide.…”

Ionic Liquids-Assisted Ring Opening of Three-Membered Heterocycles with Thio- and Seleno-Silanes

“…Only a few examples of the reaction of aziridines with chalcogen nucleophiles in ionic liquids are reported in the literature. For example, interaction of N-H aziridines with thiols proceeded efficiently in [bmim][X] (X = Cl, Br) in the absence of any catalyst [65]. β-Seleno amines can be prepared by heating aziridines with diselenides in the presence of CuO nanoparticles [66] or by use of stable zinc selenolate (PhSeZnBr) [67].…”

Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies

“…The following are available online. Synthesis of aziridines 1a–c , 4c–9c , 10 [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ], Scheme S1: Synthetic pathway for the synthesis of aziridines, Table S1: Two-Copper model, substitution of chloride with alkoxide anion: comparison of activation Free Energies corresponding to TS3 and TS4 from N -(2-picolinoyl)-methyl aziridine. Figure S1: Particular of the reaction energy profile comparison between the anti-Markovnikov and Markovnikov pathways of N -2-picolinoyl-methyl aziridine (model with the Et2O molecule), Table S2: One-Copper model, N -(2-picolinoyl)-methyl aziridine: comparison between Free Energies obtained at different theory level.…”