title: Sulfoxide-Mediated Asymmetric Synthesis of Glycosidase Inhibitor Precursors.
abstract: The highly diastereoselective DIBALH and DIBALH/ZnBr(2) reduction of enantiomerically pure (5S,(S)S)-3-ethoxy-5-(p-tolylsulfinyl)cyclopentenone (9) is used as a key step to the synthesis of oxazolidinone 2, a precursor of glycosidase inhibitor mannostatin. Compound 9 was obtained from 3-ethoxycyclopentenone by direct sulfinylation with (S)-N-benzyl-N-(p-tolylsulfinyl)propionamide.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
authors.forename: Ana B.
authors.initials: AB
authors.lastname: Bueno
authors.forename: M. Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: José L.
authors.initials: JL
authors.lastname: García Ruano
authors.forename: Ramón Gómez
authors.initials: RG
authors.lastname: Arrayás
authors.forename: María M.
authors.initials: MM
authors.lastname: Zarzuelo