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Stereospecific synthesis of eight- and nine-membered cyclic ethers by Eu(fod)3-mediated cyclization of hydroxy epoxides
Authors:Toshikazu SaitohToshio Suzuki  Norihiro OnoderaHideya Sekiguchi  Hisahiro HagiwaraTakashi Hoshi
Affiliation:a Graduate School of Science and Technology, Niigata University, 2-nocho, Ikarashi, Niigata 950-2181, Japan
b Faculty of Engineering, Niigata University, 2-nocho, Ikarashi, Niigata 950-2181, Japan
Abstract:An efficient and versatile method for the stereospecific construction of α,ω-cis- and α,ω-trans-disubstituted eight- and nine-membered cyclic ethers was developed. Cyclization of the hydroxy epoxides promoted by Eu(fod)3 proceeded via an SN2 process and exo mode to provide the corresponding cyclic ethers in excellent yields.
Keywords:cyclization   hydroxy epoxides   oxocenes   oxonenes   regioselection
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