FeCl3-Mediated Synthesis of β-Alkynyl Ketones via Domino Nucleophilic-Substitution/Intramolecular-Cyclization/Reverse Claisen Condensation of N-Cyclohexyl Propargylamines and 1,3-Diketones

J Org Chem. 2015 May 1;80(9):4760-5. doi: 10.1021/acs.joc.5b00281. Epub 2015 Apr 9.

Abstract

The synthesis of β-alkynyl ketones was achieved in good to excellent yields by an iron-catalyzed domino reaction of N-cyclohexyl propargylamines and 1,3-diketones. A plausible mechanism involving nucleophilic substitution, intramolecular cyclization, and reverse Claisen condensation for this process is proposed.