Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification

Carmela Aprile, Michelangelo Gruttadauria, Paolo Lo Meo, Serena Riela, Renato Noto

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Résumé

Eight unsaturated alcohols were cyclized by selenoetherification in 6-exo or 6-endo manner to give substituted tetrahydropyran rings. Yields, regio- and stereoselectivities were discussed in terms of steric and electronic effects such as Se-O interaction. For the first time examples of the use of silica gel in selenoetherification and the effect of the X- counter ion of PhSe+ on the reaction course are discussed. These effects are related to the occurrence of Se-O interaction.

langue originaleAnglais
Pages (de - à)293-305
Nombre de pages13
journalHeterocycles
Volume57
Numéro de publication2
Etat de la publicationPublié - 1 févr. 2002

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