Paternò-Büchi reaction between aromatic carbonyl compounds and 1-(3-furyl)alkanols

Photochem Photobiol Sci. 2008 Jan;7(1):98-103. doi: 10.1039/b716163h. Epub 2007 Nov 29.

Abstract

The photochemical reaction between aromatic carbonyl compounds and 3-furylmethanol derivatives occurs with high regioselectivity. In most of the experiments formation of oxetanes occurs at the hydroxyalkylated double bond. With chiral 1-(3-furyl)alkanols the reaction occurs with good-high stereoselectivity. In the case of 1-(3-furyl)-benzyl alcohol the stereoselectivity can be explained on the basis of the conformers of the reagent, assuming the formation of a complex between the carbonyl compound and the hydroxyl group.