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Issue 10, 2017
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Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes

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Abstract

Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with donor–acceptor (DA)-aminocyclopropanes via an ytterbium(III) catalyzed [3 + 2] annulation reaction to give tetrahydroindolizine derivatives. The products were obtained with high diastereoselectivities (dr > 20 : 1) as anti-isomers. Additionally, the formed aminals could be easily converted into secondary and tertiary amines through iminium formation followed by reduction or nucleophile addition. This transformation constitutes the first example of dearomatization of electron-poor six-membered heterocycles via [3 + 2] annulation with DA cyclopropanes.

Graphical abstract: Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes

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Publication details

The article was received on 21 Jul 2017, accepted on 24 Aug 2017 and first published on 25 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03197A
Citation: Chem. Sci., 2017,8, 7112-7118
  • Open access: Creative Commons BY-NC license
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    Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes

    J. Preindl, S. Chakrabarty and J. Waser, Chem. Sci., 2017, 8, 7112
    DOI: 10.1039/C7SC03197A

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