An unexpected highly stereoselective bisaziridination of (E,E)-1,4-dialkyl-2,3-dinitrobutadienes followed by a nitro group driven ring enlargement

摘要

(Chemical Equation Presented) (±)-2,2′-Dinitro-2,2′- biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-l,3-butadienes under verymild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3′-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.