Utilization of 1-oxa-2,2-(dimesityl)silacyclopentane acetals in the stereoselective synthesis of polyols.
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.
Powell
Sharon A
SA
Department of Chemistry, University of California, Irvine 92697-2025, USA.
Tenenbaum
Jason M
JM
Woerpel
K A
KA
D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D000080:Acetals; D000438:Alcohols; D003517:Cyclopentanes; D012821:Silanes