title: C–H bond functionalization via [1,5]-hydride shift/cyclization sequence: approach to spiroindolenines.
abstract: A concise synthesis of spiroindolenines from 2-substituted (Me, Et) indoles and 2-(pyrrolidin-1-yl)benzaldehydes has been developed via a [1,5]-hydride shift/cyclization sequence. This method features a wide substrate scope and an operationally simple procedure, affording the spiroindolenines in good to excellent yields and moderate diastereoselectivity (3.5/1 dr). When the inseparable mixture of spiroindolenine isomers were washed with isopropyl ether after flash chromatography, the major isomers could be obtained in up to >20/1 dr.
authors.forename: Peng-Fei
authors.initials: PF
authors.lastname: Wang
authors.forename: Chun-Huan
authors.initials: CH
authors.lastname: Jiang
authors.forename: Xiaoan
authors.initials: X
authors.lastname: Wen
authors.forename: Qing-Long
authors.initials: QL
authors.lastname: Xu
authors.forename: Hongbin
authors.initials: H
authors.lastname: Sun
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001547:Benzaldehydes; D007211:Indoles