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Issue 18, 2006
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Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

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Abstract

Readily prepared 2-alkyl-2-azidopropylcycloalkyl-1,3-diones undergo intramolecular Schmidt rearrangement with a range of hard Lewis acids, leading to indolizidinediones and pyrroloazepinediones. Chiral aluminium-based Lewis acids could also be used to mediate this symmetry-breaking transformation, but no significant asymmetric induction was observed.

Graphical abstract: Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

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Publication details

The article was received on 21 Jun 2006, accepted on 12 Jul 2006 and first published on 03 Aug 2006


Article type: Paper
DOI: 10.1039/B608801E
Citation: Org. Biomol. Chem., 2006,4, 3498-3504
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    Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones

    D. Lertpibulpanya and S. P. Marsden, Org. Biomol. Chem., 2006, 4, 3498
    DOI: 10.1039/B608801E

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