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Paternò-Büchi reaction between aromatic carbonyl compounds and 1-(3-furyl)alkanols
Maurizio D'Auria1, Lucia Emanuele, Rocco Racioppi
1Dipartimento di Chimica, Università della Basilicata, Via N. Sauro 85, 85100, Potenza, Italy.
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.
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