6533b86ffe1ef96bd12cdffb
RESEARCH PRODUCT
Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification
Renato NotoPaolo Lo MeoMichelangelo GruttadauriaCarmela AprileSerena Rielasubject
PharmacologySteric effectschemistry.chemical_classificationchemistry.chemical_compoundchemistrySilica gelOrganic ChemistryStereoselectivityTetrahydropyranCounterionMedicinal chemistryAnalytical Chemistrydescription
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 electroniceffects 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-01-01 |