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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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Supplementary files

Article information


Submitted
21 Jul 2017
Accepted
24 Aug 2017
First published
25 Aug 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7112-7118
Article type
Edge Article

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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