Regio- and stereoselective homocoupling of γ-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives

1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo unprecedented regio- and stereoselective homocoupling with liberation of a ketone molecule in the presence of a rhodium catalyst to give the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent cyclization of the enynes in the presence of a base affords fluorescent 2,3-dihydrofuran derivatives. Copyright © 2005 American Chemical Society.