6533b7d1fe1ef96bd125c09c

RESEARCH PRODUCT

Lipase-catalyzed resolution of anti-6-substituted 1,3-dioxepan-5-ols

Paolo Lo MeoSerena RielaFrancesco GiacaloneRenato NotoMichelangelo Gruttadauria

subject

biologyChemistryOrganic ChemistryAcetalSubstituentAlcoholTolueneCatalysisInorganic Chemistrychemistry.chemical_compoundEnantiopure drugbiology.proteinVinyl acetateOrganic chemistryPhysical and Theoretical ChemistryLipaseEnantiomer

description

Abstract Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS–C II) in toluene in the presence of vinyl acetate at 30 °C. This approach provided, in some cases, the alcohol and the acetate in high enantiomeric purity, depending on the nature of the substituent (R = N3, SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The role of the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.

yearjournalcountryeditionlanguage
2006-11-01Tetrahedron: Asymmetry
https://doi.org/10.1016/j.tetasy.2006.11.024