Department of Chemistry, Rice University, Houston, Texas 77030, United States.
Department of Chemistry and Materials Science, Aalto University, Kemistintie 1, FI-02150 Espoo, Finland.
J Am Chem Soc. 2022 Jun 22;144(24):10943-10949. doi: 10.1021/jacs.2c03805. Epub 2022 Jun 8.
A new molecular rearrangement, the -Quasi-Favorskii rearrangement, has been developed for the construction of highly substituted aziridines. Electron-deficient -sulfonyl oximes react readily with α,α-disubstituted acetophenone-derived enolates to furnish highly substituted aziridines this unprecedented domino process. In-depth computational studies reveal an asynchronous yet concerted nitrenoid-type rearrangement pathway.
一种新的分子重排反应——准福尔斯基重排反应，已被开发用于构建高度取代的氮丙啶。缺电子的 -磺酰基肟与α,α-二取代的苯乙酮衍生的烯醇盐反应，容易得到高度取代的氮丙啶——这是一个前所未有的级联反应过程。深入的计算研究揭示了一种异步但协同的氮宾型重排反应途径。
