ja027335w_si_004.pdf (1.34 MB)
Utilization of 1-Oxa-2,2-(dimesityl)silacyclopentane Acetals in the Stereoselective Synthesis of Polyols
journal contributionposted on 2002-10-02, 00:00 authored by Sharon A. Powell, Jason M. Tenenbaum, K. A. Woerpel
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.