title: Synergistic Catalysis for the Asymmetric [3+2] Cycloaddition of Vinyl Aziridines with α,β-Unsaturated Aldehydes.
abstract: The first asymmetric [3+2] cycloaddition of vinyl aziridines with α,β-unsaturated aldehydes, based on synergistic catalysis, is disclosed. This methodology allows the formation of attractive pyrrolidine structures in good yields (up to 84 %), moderate diastereoselectivity, and high enantioselectivity values (up to >99 % ee). Additionally, a tricyclic pyrrolidine core structure found in biologically active molecules was synthesized in a one-pot fashion by using the presented reaction concept. Finally, a mechanistic proposal is outlined.
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Line
authors: L
authors: Naesborg
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Fernando
authors: F
authors: Tur
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Marta
authors: M
authors: Meazza
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Jakob
authors: J
authors: Blom
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Kim Søholm
authors: KS
authors: Halskov
authors: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
authors: Karl Anker
authors: KA
authors: Jørgensen
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D010165:Palladium / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D001388:Aziridines; D011759:Pyrrolidines; D014753:Vinyl Compounds; D010165:Palladium
keywords: organocatalysis; synergistic catalysis; synthetic methods; transition-metal catalysis; vinyl aziridines