Premium
Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides
Author(s) -
Lecomte Morgan,
Evano Gwilherm
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510729
Subject(s) - electrophile , intramolecular force , chemistry , cationic polymerization , reactivity (psychology) , combinatorial chemistry , hydride , ion , simple (philosophy) , modular design , computational chemistry , stereochemistry , computer science , organic chemistry , programming language , catalysis , medicine , hydrogen , philosophy , alternative medicine , epistemology , pathology
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.