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Paper | Regular issue | Vol 57, No. 2, 2002, pp.293-305
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9404
Stereoselective Synthesis of Substituted Tetrahydropyran Rings via 6-exo and 6-endo Selenoetherification

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

*Dipartimento di Chimica Organica “E. Paternò”, Università di Palermo, Viale delle Scienze-Parco d’Orleans II, 90128 Palermo, Italy

Abstract

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.