title: Cy-SaBOX/Copper(II)-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Bicyclic N,O Acetals.
abstract: Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O-acetals is described. Cu(II) /SaBOX could catalyze the reaction of β,γ-unsaturated α-ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99 % yields; up to >95:5 d.r.; and 95-99 % ee). This reaction can be well performed on gram scale, even with only 1 mol % catalyst loading. The single-crystal structures of the copper complexes lead to a good understanding of the stereo-synergistic effects of the sidearm.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Qiong-Jie
authors.initials: QJ
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Lijia
authors.initials: L
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
authors.forename: Qi-Kai
authors.initials: QK
authors.lastname: Kang
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA. peter.zhang@bc.edu.
authors.forename: X Peter
authors.initials: XP
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China. tangy@mail.sioc.ac.cn.|Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, China. tangy@mail.sioc.ac.cn.
authors.forename: Yong
authors.initials: Y
authors.lastname: Tang
keywords: X-ray diffraction; asymmetric catalysis; copper; cycloaddition; heterocycles