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Molecules 2013, 18(9), 11384-11428; doi:10.3390/molecules180911384

Oxetane Synthesis through the Paternò-Büchi Reaction

*  and
Dipatimento di Scienze, Università della Basilicata, Viale dell'Ateneo Lucano 19, 85100 Potenza, Italy
* Author to whom correspondence should be addressed.
Received: 29 July 2013 / Revised: 5 September 2013 / Accepted: 10 September 2013 / Published: 16 September 2013
(This article belongs to the Special Issue Named Organic Reactions based on Italian Chemists)
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The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.
Keywords: photochemistry; (2+2)-cycloaddition; oxetanes; organic synthesis photochemistry; (2+2)-cycloaddition; oxetanes; organic synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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D'Auria, M.; Racioppi, R. Oxetane Synthesis through the Paternò-Büchi Reaction. Molecules 2013, 18, 11384-11428.

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