Paternò-Büchi reaction between aromatic carbonyl compounds and 1-(3-furyl)alkanols.
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.
D'Auria
Maurizio
M
Dipartimento di Chimica, Università della Basilicata, Via N. Sauro 85, 85100, Potenza, Italy.
Emanuele
Lucia
L
Racioppi
Rocco
R
Valente
Anna
A