Kinetic acidity of iminium ions. 2-Alkynyl- and 2,5-dialkynyl-pyrrolidines via the iminium ion route to azomethine ylides

Add time:07/14/2019    Source:sciencedirect.com

Condensation of carboxaldehydes with appropriate secondary propargylamines furnishes iminium ions which undergo regioselective deprotonation at the propargylic methylene group to generate azomethine ylides. Interception of the latter by N-methyl or N-phenyl maleimide furnishes 2- and 2,5-dialkynyl-pyrrolidines.

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