Malihe Javan Khoshkholgh, M. R. Hosseindokht, S. Balalaie
2012
Citations
0
Influential Citations
10
Citations
Journal
Helvetica Chimica Acta
Abstract
The CuI-catalyzed intramolecular oxa-DielsAlder reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes as unactivated terminal alkynes with 4-hydroxy-6-methyl-2H-pyran-2-one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1). A theoretical investigation of the reaction in terms of HOMOLUMO interactions in the gas phase is also reported. The reaction could be regarded as an inverse-electron-demand DielsAlder cycloaddition. The theoretical results are in high agreement with the experimental evidences.