An Unexpected Highly Stereoselective Bisaziridination of (E,E)-1,4-Dialkyl-2,3-dinitrobutadienes Followed by a Nitro Group Driven Ring Enlargement
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- 作者：Alessia Ciogli ; Stefania Fioravanti ; Francesco Gasparrini ; Lucio Pellacani ; Egon Rizzato ; Domenico Spinelli ; Paolo A. Tardella
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：December 18, 2009
- 年：2009
- 卷：74
- 期：24
- 页码：9314-9318
- 全文大小：788K
- 年卷期：v.74,no.24(December 18, 2009)
- ISSN：1520-6904
文摘
(±)-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 very mild 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.