title: Catalytic asymmetric synthesis of [2,3]-fused indoline heterocycles through inverse-electron-demand aza-Diels-Alder reaction of indoles with azoalkenes.
abstract: An unprecedented catalytic asymmetric inverse-electron-demand aza-Diels-Alder reaction of indoles with in situ formed azoalkenes is reported. A diverse set of [2,3]-fused indoline heterocycles were achieved in generally good yields (up to 97 %) with high regioselectivity and diastereoselectivity (>20:1 d.r.), and with excellent enantioselectivity (up to 99 % ee).
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China).
authors.forename: Min-Chao
authors.initials: MC
authors.lastname: Tong
authors.forename: Xuan
authors.initials: X
authors.lastname: Chen
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Rong
authors.initials: R
authors.lastname: Huang
authors.forename: Haiyan
authors.initials: H
authors.lastname: Tao
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004583:Electrons; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001372:Aza Compounds; D006571:Heterocyclic Compounds; D007211:Indoles; C057812:indoline
keywords: asymmetric catalysis; azoalkenes; cycloaddition; indoles; indolines