Stereoselective Formation of Functionalized 2,5-Dihydrofurans

Significance

Optically active starting materials are smoothly converted into the corresponding 2,5-dihydrofurans with high levels of chirality transfer. Primary, secondary, and tertiary alcohol groups gave high yields in all cases. For the reaction using chiral starting materials, only the primary alcohols did not show high chirality transfer. The reaction proceeds through an allenyl intermediate which is cyclized by the gold(I) catalyst to generate the product.