27593-56-2Relevant articles and documents
Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (Z)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange: Stereoselective Synthesis of 2-Acylaziridines
Ochiai, Masahito,Kitagawa, Yutaka
, p. 3181 - 3189 (2007/10/03)
Monocarbonyl iodonium ylides, generated in situ from (Z)-(2-acetoxyvinyl)iodonium salts via an ester exchange reaction with EtOLi, undergo alkylidene transfer reactions to activated imines yielding 2-acylaziridines in good yields. The stereochemical outcome of this aziridination was shown to be dependent on both the activating groups of the imines and the reaction solvents: that is, the aziridination of N-(2,4,6-trimethylbenzenesulfonyl)imines in THF affords cis-aziridines as a major product while that of N-benzoylimines in THF-DMSO or THF gives the trans isomer stereoselectively.