6533b85efe1ef96bd12bfc9c

RESEARCH PRODUCT

Lipase-catalyzed resolution of β-hydroxy selenides

Paolo Lo MeoRenato NotoSerena RielaMichelangelo GruttadauriaFrancesca D'anna

subject

lipase stereoselective reaction beta hydroxy selenidesbiologyOrganic ChemistrySettore CHIM/06 - Chimica OrganicaTolueneCatalysisCatalysisInorganic Chemistrychemistry.chemical_compoundEnantiopure drugchemistrySelenidebiology.proteinVinyl acetateOrganic chemistryPhysical and Theoretical ChemistryEnantiomerLipaseEnantiomeric excess

description

Abstract Eleven β-hydroxy selenides 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 several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic β-hydroxy selenides is also discussed. Enantiopure β-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1 S ,2 R )-indene oxide was obtained in one step from the proper enantiopure β-hydroxy selenide.

yearjournalcountryeditionlanguage
2006-10-01Tetrahedron: Asymmetry
https://doi.org/10.1016/j.tetasy.2006.10.010