103723-92-8Relevant articles and documents
Iron-Catalyzed Intra-intermolecular Aminoazidation of Alkenes
Fayssal, Sandra Abi,Giungi, Alessandro,Berhal, Farouk,Prestat, Guillaume
, p. 695 - 703 (2020)
An intra-intermolecular iron-catalyzed aminoazidation of non-activated alkenes is reported for the preparation of imidazolidinone, oxazolidinone, and pyrrolidinone derivatives. The method uses cheap and abundant iron as a catalyst and commercially available TMSN3 as an azide source. This domino process allows, in a single operating step, for a ring-closure that generates an aza-heterocycle and the introduction of an azido appendage tethered to the heterocycle. The conditions developed offer a sustainable alternative method for the preparation of unsymmetrical vicinal diamine compounds.
Iron(II)-catalyzed intramolecular aminohydroxylation of olefins with functionalized hydroxylamines
Liu, Guan-Sai,Zhang, Yong-Qiang,Yuan, Yong-An,Xu, Hao
supporting information, p. 3343 - 3346 (2013/04/23)
A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.
Copper-catalyzed tethered aziridination of unsaturated N-tosyloxy carbamates
Liu, Renmao,Herron, Steven R.,Fleming, Steven A.
, p. 5587 - 5591 (2008/02/09)
(Chemical Equation Presented) Aziridines were formed by copper-catalyzed intramolecular nitrene addition to alkenes. The carbamate group was used as the tether between the alkene and the nitrene. Subsequent nucleophilic attack of the aziridine was accomplished using RSH, R2NH, N3 -, or ROH as the nucleophile. This addition was found to be regio- and stereoselective. This methodology has been used to demonstrate its utility in the regio-and stereoselective synthesis of a 1,2-diamino-3- hydroxycyclohexane. This substitution pattern is found in natural products such as Tamiflu.