title: Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols.
abstract: We have developed a route for the stereoselective synthesis of 1-oxa-2,2-(dimesityl)silacyclopentane acetals, intermediates in the synthesis of highly functionalized 1,3-diols. This route involves a diastereoselective conjugate addition reaction of a hydrosilyl anion, a subsequent diastereoselective enolate alkylation, and a fluoride-catalyzed intramolecular hydrosilylation reaction to afford the oxasilacyclopentane acetal. A highly selective nucleophilic substitution reaction, followed by oxidation of the C-Si bond, leads to the desired polyol.
authors.affiliation: Department of Chemistry, University of California, Irvine 92697-2025, USA.
authors.forename: Sharon A
authors.initials: SA
authors.lastname: Powell
authors.forename: Jason M
authors.initials: JM
authors.lastname: Tenenbaum
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
chemical_list: D000080:Acetals; D000438:Alcohols; D003517:Cyclopentanes; D012821:Silanes