Abstract
The Paterno-Buchi reaction on furan derivatives is reviewed. The photochemical reaction of furan derivatives in the reaction with carbonyl compounds gives the corresponding monoadduct with high regio- and stereoselectivity. When the reaction is carried out in benzene, a large amount of the diadduct can be obtained. The exo stereoselectivity at C-6 was explained assuming the presence of a secondary orbital effect on spin orbit coupling. Regio- and stereoselectivity of the reaction of carbonyl compounds with 2,3-dihydrofuran is described. Applications of the reaction to the synthesis of 2- and 3-furylmethanol derivatives is reported. The synthesis of asteltoxin, avenaciolide, and oxetanocin is also reported. Asymmetric reactions on chiral glyoxylate is reported. The low diastereoselectivity of the reaction with chiral ketones and aldehydes is discussed. Finally, the high diastereoselectivity observed in the reaction with 2-furylmethanol derivatives is reported.
Keywords: Paterno-Buchi, 2-furylmethanol, 2,3-dihydrofuran
Current Organic Chemistry
Title: The Paterno-Buchi Reaction on Furan Derivatives
Volume: 7 Issue: 14
Author(s): M. D'Auria, L. Emanuele, R. Racioppi and G. Romaniello
Affiliation:
Keywords: Paterno-Buchi, 2-furylmethanol, 2,3-dihydrofuran
Abstract: The Paterno-Buchi reaction on furan derivatives is reviewed. The photochemical reaction of furan derivatives in the reaction with carbonyl compounds gives the corresponding monoadduct with high regio- and stereoselectivity. When the reaction is carried out in benzene, a large amount of the diadduct can be obtained. The exo stereoselectivity at C-6 was explained assuming the presence of a secondary orbital effect on spin orbit coupling. Regio- and stereoselectivity of the reaction of carbonyl compounds with 2,3-dihydrofuran is described. Applications of the reaction to the synthesis of 2- and 3-furylmethanol derivatives is reported. The synthesis of asteltoxin, avenaciolide, and oxetanocin is also reported. Asymmetric reactions on chiral glyoxylate is reported. The low diastereoselectivity of the reaction with chiral ketones and aldehydes is discussed. Finally, the high diastereoselectivity observed in the reaction with 2-furylmethanol derivatives is reported.
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Cite this article as:
D'Auria M., Emanuele L., Racioppi R. and Romaniello G., The Paterno-Buchi Reaction on Furan Derivatives, Current Organic Chemistry 2003; 7 (14) . https://dx.doi.org/10.2174/1385272033486378
DOI https://dx.doi.org/10.2174/1385272033486378 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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