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Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence

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Abstract

An organocatalysis triggered highly regio- and stereoselective two-step sequence between hemiacetals and indole-containing nitroolefins was developed. The key to the success of this sequence was the intramolecular oxocarbenium ion induced collective alkylation at the C3, C2, or N1-position of the indole moiety, respectively, providing biologically important polycyclic indole derivatives with different ring connectivities. An unexpected epimerization was observed during the C3-alkylation process, which generated products with different relative configurations compared with the C2- and N1-alkylation products.

Graphical abstract: Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence

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Publication details

The article was received on 25 Dec 2018, accepted on 08 Feb 2019 and first published on 12 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QO01406J
Citation: Org. Chem. Front., 2019, Advance Article

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    Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence

    C. Xie, R. Tan and Y. Liu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01406J

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