857048-92-1Relevant articles and documents
Gold catalysis: Dihydroisobenzofurans and isochromanes by the intramolecular furan/alkyne reaction
Stephen,Hashmi,Woelfle,Ata, Filiz,Hamzic, Melissa,Salathe, Ralph,Frey, Wolfgang
, p. 2501 - 2508 (2006)
A series of furyl alcohols and homofuryl alcohols was synthesized by reduction of furfurals or reaction of furyllithium compounds with epoxides and subsequent propargylation. The gold-catalyzed cycloisomerization of these products furnished dihydroisobenzofurans and isochromanes. Crystal structure analyses proved the sequence of the substituents for both classes of products. Unsaturated dicarbonyl compounds as side-products show the mechanistic relationship to the analogous platinum-catalyzed reactions. Neither ester groups, even on the 4-position of the furan ring, nor aryl bromides hinder the catalysis by gold. In the case of a substrate with an allyl ether in the side chain, a side-product, which provides evidence for a reaction of the alkyne with an inverse regioselectivity, was observed.