Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides |
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| Authors: | Morgan Lecomte Prof. Gwilherm Evano |
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| Affiliation: | Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Bruxelles, Belgium |
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| Abstract: | An efficient, modular and straightforward entry to tetrahydropyridines and piperidines is reported. This reaction is based on a formal intramolecular hydroalkylation of readily available, properly substituted ynamides which, upon simple activation under acidic conditions, generate highly reactive activated keteniminium ions whose reactivity can be finely controlled to induce a remarkably efficient [1,5]‐hydride shift from unactivated C?H bonds and trigger a cationic cyclization which is complete within minutes. |
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| Keywords: | cationic cyclizations hydride shift keteniminium ions piperidines ynamides |
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