Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

Journal of the American Chemical Society
Qi XingWing-Yiu Yu

Abstract

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the C═C and C≡C bonds.

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Citations

Nov 7, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Linhong ZuoWusheng Guo
Apr 10, 2021·Journal of the American Chemical Society·Xiang LyuSukbok Chang
Apr 23, 2021·Journal of the American Chemical Society·Euijae LeeSukbok Chang
Aug 27, 2019·Journal of the American Chemical Society·Hoimin JungSukbok Chang
May 2, 2020·Organic Letters·Masaki YoshitakeTatsuya Uchida
Oct 18, 2019·Journal of the American Chemical Society·Yang HuX Peter Zhang
Apr 21, 2020·Journal of the American Chemical Society·Yeongyu HwangSukbok Chang
Dec 1, 2020·Journal of the American Chemical Society·Kai LangX Peter Zhang
Feb 28, 2020·The Journal of Organic Chemistry·Jitian LiuXiaoxun Li
Jul 14, 2020·Journal of the American Chemical Society·Minsoo JuJennifer M Schomaker
Mar 5, 2020·Journal of the American Chemical Society·Hoimin JungSukbok Chang
Dec 28, 2019·Journal of the American Chemical Society·Marco CianfanelliMiquel Costas
Apr 13, 2019·Journal of the American Chemical Society·Hao WangGong Chen
Aug 28, 2020·Journal of the American Chemical Society·Xianqing WuYifeng Chen
Sep 18, 2021·Angewandte Chemie·Soumitra V AthavaleFrances H Arnold
Dec 17, 2021·Journal of the American Chemical Society·Shuang LiuJin-Quan Yu
Dec 24, 2021·Journal of the American Chemical Society·Zhen LiuFrances H Arnold

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