147054-74-8Relevant articles and documents
Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: Are they under kinetic or thermodynamic control?
Aggarwal, Varinder K.,Charmant, Jonathan P.H.,Ciampi, Cinzia,Hornby, Jonathan M.,O'Brien, Christopher J.,Hynd, George,Parsons, Richard
, p. 3159 - 3166 (2001)
Sulfur ylides react with imines, via betaines, to give aziridines. We sought to determine whether betaine formation was reversible in reactions of benzyl-, amide- and ester-stabilised ylides by carrying out cross-over experiments. Thus, the intermediate betaines were generated independently from the corresponding sulfonium salt in the presence of a more reactive imine (p-nitrobenzaldimine). It was found that no incorporation of the more reactive imine was observed in reactions with the benzyl-stabilised ylide, whilst >80% incorporation of the p-nitrobenzaldimine was observed from the ester- and amide-stabilised ylides. These results indicate that benzyl-stabilised ylides react irreversibly with imines but ester- and amide-stabilised react reversibly. Thus, the stereocontrolling step of the process is dependent on the type of ylide employed and the results are used to account for the different diastereoselectivities observed with the different ylides.
A facile C-arylation of N-tosyl aziridines via Ag(I) catalysis
Bera, Milan,Roy, Sujit
, p. 7144 - 7146 (2007)
N-Tosyl aziridines react with a variety of arenes and heteroarenes in the presence of 1-2% of silver hexafluorophosphate at room temperature to afford the corresponding β-aryl amine derivatives in excellent yields and with high regioselectivity.
Chiral bis(pyrazolyl)methane copper(I) complexes and their application in nitrene transfer reactions
Thomas, Fabian,Steden, Dominik,Eith, Alexander,Hoffmann, Alexander,Herres-Pawlis, Sonja
, p. 835 - 847 (2021/11/09)
In this study, chiral bis(pyrazolyl)methane copper(I) acetonitrile complexes were applied to generate two novel terminal copper tosyl nitrene complexes with the nitrene generating agent SPhINTs in dichloromethane at low temperatures. The syntheses of the chiral bis(pyrazolyl)methane ligands are based on pulegone and camphor, members of the natural chiral pool. The chiral copper(I) acetonitrile complexes were applied as catalysts in the copper nitrene mediated aziridination reaction of different styrene derivatives and the C-H amination of various substrates. The reactions afforded good yields, but low enantiomeric excess under mild conditions. The nitrene species have been characterized with UV/Vis and EPR spectroscopy and the products of the decay by ESI mass spectrometry.
Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources
Berhal, Farouk,Grimaud, Laurence,Kirby, Georgina,Prestat, Guillaume,Vitale, Maxime R.
, p. 9428 - 9432 (2021/12/09)
The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is
