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Phenylselenoetherification of some Δ4-alkenols facilitated by pyridine and some Lewis acids

✍ Scribed by Biljana M. Šmit; Zorica M. Bugarčić

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
84 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image Studies on the phenylselenoetherification of some Δ^4^‐alkenols in the presence of pyridine and some Lewis acids are described. All alkenols underwent intramolecular cyclization yielding corresponding tetrahydrofuran or tetrahydropyran derivatives. Yield and diastereomeric ratio of the cyclic products depend on counterion of selenylating reagent used. We found that external additives, such as pyridine and some Lewis acids coordinating to the electrophilic and/or nucleophilic species are used to control the course of cyclizations with high degrees of efficiency and improve the level of stereoinduction. J. Heterocyclic Chem., (2010).

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