TFP as a ligand in Au(I)-catalyzed dihydropyran synthesis. Unprecedented rearrangement of dihydropyrans into cyclopentenones

Abstract

Dihydropyrans have been prepared by the cyclisation of easily accessible propargyl vinyl ethers with (TFP) AuCl/AgBF(4) as a catalyst in high yields. These compounds undergo acid-catalysed rearrangement into cyclopentenone derivatives.

Keywords

• cationic gold(I) complexes
• Claisen rearrangement
• alpha-alkenylation
• organic-synthesis
• domino reactions
• enynes
• cyclization
• cycloadditions
• 1,5-enynes
• catalysis