340184-74-9Relevant articles and documents
Hydroxy-directed, fluoride-catalyzed epoxide hydrosilylation for the synthesis of 1,4-diols
Zhang, Yong-Qiang,Funken, Nico,Winterscheid, Peter,Gans?uer, Andreas
supporting information, p. 6931 - 6934 (2015/06/08)
Abstract A novel highly regioselective, fluoride-catalyzed hydrosilylation of β-hydroxy epoxides has been developed. The reaction is modular and applicable to the synthesis of a broad range of 1,4-diols. Fluoride is crucial for two reasons: First, it promotes the formation of a silyl ether (which contains a Si-H bond) and, second, it enables ring opening by an intramolecular SN2 reaction through activation of the silane. The reaction can be performed under air. A modular, convergent, and stereoselective synthesis of 1,4-diols by epoxide hydrosilylation has been developed (see scheme). The reaction occurs under fluoride catalysis, is high yielding, highly regioselective, and can be carried out on a large scale.
Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4
Chirskaya,Vasil'ev,Shorshnev,Sviridov
, p. 1300 - 1303 (2008/02/05)
Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generat
