Gold Catalysis: Desymmetrization in the Furan-Yne Reaction

Abstract

A series of seven symmetric difuryl-diynes were synthesized by a route delivering an anti-configurated product as the major product. The gold-catalyzed conversion of the individual anti- and syn-diastereomers was investigated. The anti-diastereomer in a desymmetrization reaction chemoselectively delivered dihydro­indenediols with a furyl and a 2-oxopropyl side chain. The syn-dia­stereomer was completely converted into oligomeric/polymeric material. Thus, it was not necessary to separate the minor amount of the syn-diastereomers from the product mixtures in order to isolate the dihydroindenediols.