6533b838fe1ef96bd12a47ea
RESEARCH PRODUCT
Synthesis of 2,4,6-trisubstituted tetrahydropyrans via 6-exo selenoetherification of unsaturated alcohols
Michelangelo GruttadauriaCarmela AprileRenato NotoSerena Rielasubject
inorganic chemicalsSilica gelOrganic ChemistryRegioselectivityTetrahydropyranRing (chemistry)Biochemistrychemistry.chemical_compoundOxygen atomchemistryDrug Discoverypolycyclic compoundsOrganic chemistrytetrahydropyranStereoselectivitydescription
Stereoselectivity, regioselectivity and yields in the 6-exo selenoetherification of four unsaturated diols were found to depend on the stereochemistry of the diols and on the presence of an oxygen atom close to the intermediate seleniranium ring. Silica gel was useful in order to obtain good yields. Reactions performed both under kinetic and thermodynamic control led to the same products. Stereoselectivity, regioselectivity and yields in the 6-exo selenoetherification of four unsaturated diols were found to depend on several factors such as the stereochemistry of the diols, the nature of the R group, the nature of the counter anion of the PhSe+ species and the presence of silica gel.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-03-01 | Tetrahedron Letters |