title: Synthesis of Differentially Protected myo- and chiro-Inositols from D-Xylose; Stereoselectivity in Intramolecular SmI(2)-Promoted Pinacol Reactions.
abstract: Methods for the enantioselective conversion of D-xylose to differentially protected myo-inositol and L-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI(2)-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explanations for this behavior are discussed.
authors.affiliation: Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Luchetti
authors.forename: Kejia
authors.initials: K
authors.lastname: Ding
authors.forename: Alexander
authors.initials: A
authors.lastname: Kornienko
authors.forename: Marc
authors.initials: M
authors.lastname: d'Alarcao