96185-38-5Relevant academic research and scientific papers
Ring-opening of NH-aziridines with thiols in ionic liquids: Application to the synthesis of aminosulfide catalysts for asymmetric epoxidation of aldehydes
Namutebi, Mariam,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
experimental part, p. 1250 - 1272 (2010/08/21)
The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3- methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction. Copyright Taylor & Francis Group.
Synthesis of mexiletine analogues from non-activated aziridines
Ingebrigtsen, Truls,Lejon, Tore
, p. 891 - 902 (2008/03/13)
A general method for the synthesis of mexiletine analogues by nucleophilic ring opening of non-activated racemic aziridines has been developed (Scheme 1). Structural variation is introduced by employing different nucleophiles or by altering the substitution on the aziridine ring.
Synthesis and evaluation of N,S-compounds as chiral ligands for transfer hydrogenation of acetophenone
Ekegren, Jenny K.,Roth, Peter,Kaellstroem, Klas,Tarnai, Tibor,Andersson, Pher G.
, p. 358 - 366 (2007/10/03)
New nitrogen- and sulfur-containing compounds, bicyclic and monocyclic, were prepared and evaluated as ligands in the transfer hydrogenation of acetophenone. Utilising [Ir(COD)Cl]2 as metal precursor the best result, 80% ee, was obtained using
β-Functionalized Hydrazines from N-Phthalimidoaziridines and their Hydrogenolytic N,N-Cleavage to Amines
Egli, Marcus,Hoesch, Lienhard,Dreiding, Andre S.
, p. 220 - 230 (2007/10/02)
The three N-phthalimido-aziridines 1-3 were reacted with phenol, thiophenol, aniline, p-toluenesulfonic acid, and H2O in selected combinations.These nucleophiles opened the 3-membered ring to yield the N-phthalimidoamines 4a-d, 5a-d, 6a-c, and 6e; all these products (except the carbinol 6e) carry an aryl-substituted functional group on the C-atom vicinal to the N-substituent.Hydrazonolysis of 4, 5, 6a-c afforded the β-functionalized hydrazines 7, 8, 9a-c, and 9e.The reducing medium Raney-Ni/N2H4 transformed 4, 5, 6a-c, and 6e to the β-functionalized amines, 10, 11, 12a-c, and 12e.By a study with the hydrazide 6a and the hydrazine 9a, it was shown that the N,N-cleavage is a catalytic hydrogenolysis by H2 generated from N2H4 with Raney-Ni and that it does not take place on the hydrazide 6, but rather on the hydrazine 9, generated as intermediate from 6 with N2H4.Spectroscopic data confirmed that the conversions of 1-3 to 4-6 occurred exclusively with inversion and that the resulting configuration remained fully intact during the transformations of 4, 5, and 6 (via 7, 8, and 9) to 10, 11, and 12, respectively.
