Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides. (2nd March 2016)

• Record Type: Journal Article
• Authors: Lecomte, Morgan; Evano, Gwilherm
• Is Part Of: Angewandte Chemie. Volume 128:Number 14(2016)
• Page Start: 4623
• Page End: 4627
• Publication Date: 2016-03-02
• Subjects: Hydridverschiebungen -- Inamide -- Kationische Cyclisierungen -- Keteniminiumionen -- Piperidine; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201510729
• Languages: English
• ISSNs: 0044-8249

Abstract

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.