Au-Catalyzed Synthesis of 5,6-Dihydro-8H-indolizin-7-ones from N-(Pent-2-en-4-ynyl)-β-lactams
Organic Letters2008Vol. 10(22), pp. 5187–5190
Citations Over TimeTop 10% of 2008 papers
Abstract
Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.
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