title: Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction.
abstract: An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N'-dioxide-Sc(III) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19 : 1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.
authors: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. xmfeng@scu.edu.cn.
authors: Haipeng
authors: H
authors: Hu
authors: Yangbin
authors: Y
authors: Liu
authors: Jing
authors: J
authors: Guo
authors: Lili
authors: L
authors: Lin
authors: Yali
authors: Y
authors: Xu
authors: Xiaohua
authors: X
authors: Liu
authors: Xiaoming
authors: X
authors: Feng
mesh_terms: D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004583:Electrons; D007783:Lactones / Q000737:chemistry; D011809:Quinones / Q000737:chemistry; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D056831:Coordination Complexes; D003374:Coumarins; D007783:Lactones; D011809:Quinones; D012538:Scandium