title: Highly diastereo- and enantioselective palladium-catalyzed [3+2] cycloaddition of vinyl aziridines and α,β-unsaturated ketones.
abstract: A palladium-catalyzed asymmetric [3+2] cycloaddition reaction of vinylaziridines with α,β-unsaturated ketones, wherein the alkenes have a single activator, is realized in high diastereo- and enantioselectivity, thus affording 3,4-disubstituted pyrrolidines in high yields with excellent ee values. The introduction of a methyl group at C1 of the vinyl group the vinylaziridines greatly improves the stereochemistry of the reaction. A plausible transition state is proposed.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), 345 Lingling Road, Shanghai 200032 (China).
authors.forename: Chao-Fan
authors.initials: CF
authors.lastname: Xu
authors.forename: Bao-Hui
authors.initials: BH
authors.lastname: Zheng
authors.forename: Jia-Jia
authors.initials: JJ
authors.lastname: Suo
authors.forename: Chang-Hua
authors.initials: CH
authors.lastname: Ding
authors.forename: Xue-Long
authors.initials: XL
authors.lastname: Hou
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D007659:Ketones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001388:Aziridines; D007659:Ketones; D010165:Palladium
keywords: asymmetric catalysis; cycloaddition; heterocycles; palladium; synthetic methods