Imino Corey-Chaykovsky reaction

Aziridines can also be synthesized enantioselectively from imines and alkyl halides using a camphor-derived chiral sulfide mediator 640 in a one-pot procedure via the imino Corey-Chaykovsky reaction. Thus, benzyl bromide 641 and tosyl imine 642 provide aziridine 643 in practically quantitative yield as a 3 1 mixture of ( /Z)-isomers and in 92% ee ((i4)-isomer) (Scheme 157). An electron-withdrawing substituent on the imine nitrogen is necessary to activate the 7t-system for nucleophilic attack <2001TL5451>. 

Salto, T., Sakairi, M., Akiba, D. Enantioselective synthesis of aziridines from imines and alkyl halides using a camphor-derived chiral sulfide mediator via the imino Corey-Chaykovsky reaction. Tetrahedron Lett. 2001,42, 5451-5454. 

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