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

Article abstract of DOI:10.1039/b608801e

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. The Royal Society of Chemistry 2006.