49790-76-3Relevant articles and documents
Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions
Redlich, Mark,Hossain, M. Mahmun
, p. 8987 - 8990 (2007/10/03)
The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines: A highly diastereoselective synthesis of cis-aziridine carboxylates
Sengupta,Mondal
, p. 6245 - 6248 (2007/10/03)
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines give aziridine carboxylates under mild conditions, low catalyst loading and with high cis-selectivity. (C) 2000 Elsevier Science Ltd.
Catalytic formation of aziridines from imines. Characterisation of an intermediate in SnCl4-catalysed aziridination and mechanistic considerations
Rasmussen, Kaare G.,Juhl, Karsten,Hazell, Rita G.,Jorgensen, Karl Anker
, p. 1347 - 1350 (2007/10/03)
The tin(IV) catalysed aziridination of imines using ethyl diazoacetate as the carbene fragment donor has been investigated from a synthetic and mechanistic point of view. For imines substituted with aromatic substituents, an intermediate in the aziridination reaction has been isolated and characterised by X-ray diffraction. This intermediate is an octahedral complex with a trans coordination of two imines and in which the imines have isomerised from trans to cis by the reaction with/coordination to tin(iv). Tin(IV) is a very effective catalyst for the aziridination of various imines giving cis-aziridines as the major product. The aziridination can proceed with a very low catalyst load as 0.05 mol% of SnCl4 is sufficient to achieve a high conversion. For the formation of aziridines a linear plot of the experimental data is obtained by means of the Hammett equation for a series of competition experiments. Based on the results the mechanism for the aziridination is discussed in terms of a Lewis acid activation of the imine for a nucleophilic attack of ethyl diazoacetate.
