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Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

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Abstract

We reported a highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes via cationic Rh(I) catalysis in this context. The combination of various secondary amines and indoles with keto-vinylidenecyclopropanes afforded the corresponding hydrofunctionalization products in good to excellent yields with outstanding ee values under mild conditions. A new TMM–Rh model complex was proposed, providing an atom economical Rh-π-allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

Graphical abstract: Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

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Publication details

The article was received on 08 Apr 2018, accepted on 09 May 2018 and first published on 11 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01595C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

    S. Yang, Q. Li, C. Xu, Q. Xu and M. Shi, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC01595C

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