A joint experimental and ab initio study on the reactivity of several hydroxy selenides. Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

Michelangelo Gruttadauria, Carmela Aprile, Francesca D'Anna, Paolo Lo Meo, Serena Riela, Renato Noto

Research output: Contribution to journalArticlepeer-review

Abstract

The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to get a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given.

Original languageEnglish
Pages (from-to)6815-6822
Number of pages8
JournalTetrahedron
Volume57
Issue number31
DOIs
Publication statusPublished - 30 Jul 2001
Externally publishedYes

Keywords

  • Cyclizations
  • Oxygen heterocycles
  • Selenium
  • Theoretical studies

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