title: Catalytic asymmetric [3+2] cycloaddition of aromatic aldehydes with oxiranes by C-C bond cleavage of epoxides: highly efficient synthesis of chiral 1,3-dioxolanes.
abstract: A novel and efficient N,N'-dioxide-Gd(III) complex was developed for the highly diastereo- and enantioselective [3+2] cycloaddition of aryl oxiranyl diketones and aldehydes via C-C bond cleavage of oxiranes. The corresponding chiral 1,3-dioxolanes were obtained in excellent yields (up to 99%) with high diastereoselectivities (>95 : 5 dr) and enantioselectivities (up to 91% ee). Moreover, a possible transition model was proposed to explain the origin of the asymmetric induction.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. xmfeng@scu.edu.cn.
authors.forename: Weiliang
authors.initials: W
authors.lastname: Chen
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Cai
authors.forename: Yong
authors.initials: Y
authors.lastname: Xia
authors.forename: Weidi
authors.initials: W
authors.lastname: Cao
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004148:Dioxolanes / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D056831:Coordination Complexes; D004148:Dioxolanes; D004852:Epoxy Compounds; D007659:Ketones; D002244:Carbon; D005682:Gadolinium; C010962:formal glycol