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 stereosele...

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Bibliographic Details
Published in:Photochemical & photobiological sciences 2008-01, Vol.7 (1), p.98-103
Main Authors: D’Auria, Maurizio, Emanuele, Lucia, Racioppi, Rocco, Valente, Anna
Format: Article
Language:English
Subjects:
Biochemistry
Biomaterials
Chemistry
Physical Chemistry
Plant Sciences
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Summary: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.
ISSN:1474-905X
1474-9092
DOI:10.1039/b716163h