10282-18-5Relevant articles and documents
Exocyclic iminium salts as catalysts for alkene epoxidation by Oxoneρ
Armstrong, Alan,Ahmed, Ghafoor,Garnett, Ian,Goacolou, Katell,Wailes, J. Steven
, p. 2341 - 2352 (1999)
Exocyclic iminium salts are evaluated as catalysts for alkene epoxidation by Oxone, presumed to proceed via the corresponding oxaziridinium species. Iminium triflate salts derived from pyrrolidine and electron poor aromatic aldehydes were found to be good catalysts. Attempts to prepare chiral variants of these iminium salts were largely unsuccessful, presumably due to their ready hydrolysis.
Formation of epoxides and N-arylaziridines via a simple Mg-Barbier reaction in DMF
Oudeyer, Sylvain,Léonel, Eric,Paugam, Jean Paul,Nédélec, Jean-Yves
, p. 919 - 923 (2014)
The Mg-activation of benzal bromide 2b in DMF in the presence of carbonyl compounds 1 or imines 4 leads to epoxides 3 and N-arylaziridines 5, respectively, with acceptable isolated yields. It was found that DMF is likely involved in this process to form a nucleophilic intermediate by reaction with a first generated electrophilic carbene. Results obtained in this chemical approach are compared to those obtained using electrochemical activation, also in DMF.
Non-aqueous iminium salt mediated catalytic asymmetric epoxidation
Bulman Page, Philip C.,Buckley, Benjamin R.,Barros, David,Blacker, A. John,Heaney, Harry,Marples, Brian A.
, p. 6607 - 6613 (2006)
A range of substituted dihydroisoquinolinium salts has been tested in the catalytic asymmetric epoxidation of simple alkenes using our newly developed non-aqueous conditions employing tetraphenylphosphonium monoperoxysulfate (TPPP) as oxidant, giving ees of up to 97%.
Highly efficient catalysts for epoxidation mediated by iminium salts
Bulman Page, Philip C.,Buckley, Benjamin R.,Appleby, Louise F.,Alsters, Paul A.
, p. 3405 - 3411 (2005)
A range of substituted dihydroisoquinolinium salts has been tested in the catalytic epoxidation of several alkenes. Catalyst loadings as low as 0.5 mol% have been used in the epoxidation of 1-phenylcyclohexene. Georg Thieme Verlag Stuttgart.
A biomimetic iron catalyst for the epoxidation of olefins with molecular oxygen at room temperature
Schroeder, Kristin,Join, Benoet,Amali, Arlin Jose,Junge, Kathrin,Ribas, Xavi,Costas, Miquel,Beller, Matthias
, p. 1425 - 1429 (2011)
It's no sacrifice: A bio-inspired iron system, in which a β-keto ester serves as a sacrificial cosubstrate, readily epoxidizes olefins under ambient conditions with air. Aromatic olefins are oxidized in high yields with excellent chemoselectivity. Mechanistic investigations point out substantial differences to well-known radical-based autoxidations.
Manganese salen compounds embedded within cross-linked chiral polyethylenimine: Asymmetric epoxidation in an aqueous biphasic medium
Levi, Noam,Neumann, Ronny
, p. 977 - 981 (2012)
Chiral cross-linked polyethylenimines were used to intercalate MnIII salen catalysts, thereby inducing a chiral environment upon an achiral metal complex. The synzyme, dispersed in water, catalyzes the aqueous biphasic asymmetric epoxidation of styrene de
Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides
Lee, Jeong Min,Bae, Dae Young,Park, Jin Yong,Jo, Hwi Yul,Lee, Eunsung,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 4608 - 4613 (2020/06/05)
A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.
Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines
Cabré, Albert,Cabezas-Giménez, Juanjo,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier,Lledós, Agustí,Riera, Antoni
supporting information, p. 3624 - 3631 (2019/07/10)
The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).
