Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones.
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.
Lertpibulpanya
Duanpen
D
Department of Chemistry, Imperial College, London, UK SW7 2AY.
Marsden
Stephen P
SP
D001381:Azepines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D007212:Indolizines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D011758:Pyrroles / Q000737:chemistry*
D001381:Azepines; D001386:Azides; D007212:Indolizines; D007659:Ketones; D011758:Pyrroles