Synthesis of fluorinated 2,3-dihydropyran-4-ones by cyclocondensation of 1,3-dicarbonyl dianions with aldehydes

The reaction of the dianion of 1,1,1-trifluoro-pentane-2,4-dione with aldehydes and subsequent addition of hydrochloric acid afforded 2,3-dihydro-6-trifluoromethyl-pyran-4-ones. The reaction of the dianion of acetylacetone with fluorinated benzaldehydes gave the corresponding fluorinated 2-aryl-2,3-dihydro-6-methyl-pyran-4-ones. All reactions proceeded in very good yield and with very good regioselectivity.

Graphical abstractFluorinated 2,3-dihydro-4H-pyran-4-ones are prepared by cyclocondensation of 1,3-dicarbonyl dianions with aldehydes.Figure optionsDownload full-size imageDownload as PowerPoint slide