title: Dysprosium(III)-Catalyzed Ring-Opening of meso-Epoxides: Desymmetrization by Remote Stereocontrol in a Thiolysis/Elimination Sequence.
abstract: An unprecedented asymmetric desymmetrization of meso-epoxides, derived from cyclopentene-1,3-diones, with 2-mercaptobenzothiazoles has been realized. It was efficiently catalyzed by a chiral Dy(III) /N,N'-dioxide complex through a thiolysis/elimination sequence. This remote stereocontrol strategy provides facile access to synthetically versatile cyclopentene derivatives bearing an all-carbon quaternary stereogenic center in high yield and excellent enantioselectivity. Intriguingly, optically active thiophene could be readily generated from the obtained product through an efficient one-pot protocol.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
authors.forename: Lu
authors.initials: L
authors.lastname: Yao
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
authors.forename: Qiao
authors.initials: Q
authors.lastname: Zhu
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
authors.forename: Liang
authors.initials: L
authors.lastname: Wei
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
authors.forename: Zuo-Fei
authors.initials: ZF
authors.lastname: Wang
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China. cjwang@whu.edu.cn.|State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China. cjwang@whu.edu.cn.
authors.forename: Chun-Jiang
authors.identifier: 0000-0003-3629-6889
authors.initials: CJ
authors.lastname: Wang
keywords: N ligands; asymmetric catalysis; dysprosium; enantioselectivity; heterocycles