title: Synergistic Diastereo- and Enantioselective Functionalization of Unactivated Alkyl Quinolines with α,β-Unsaturated Aldehydes.
abstract: A novel alkyl functionalization of unactivated alkyl quinolines has been developed combining InCl3activation with organocatalytic activation of α,β-unsaturated aldehydes in a synergistic fashion. The reaction proceeds in a highly stereoselective manner as a sequence involving two consecutive synergistic catalytic cycles (Lewis acid- and iminium ion-catalyzed) and requires neither pre-activated alkyl quinoline substrates with electron-withdrawing substituents nor highly activated electrophiles. The reaction provides selectively double- or mono-addition products in good yields and high to excellent stereoselectivities. Furthermore, based on spectroscopic and labelling experiments, the mechanisms for the reactions are discussed.
authors.affiliation: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors.forename: Marta
authors.initials: M
authors.lastname: Meazza
authors.affiliation: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors.forename: Fernando
authors.initials: F
authors.lastname: Tur
authors.affiliation: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors.forename: Niels
authors.initials: N
authors.lastname: Hammer
authors.affiliation: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
keywords: asymmetric catalysis; heterocycles; indium; organocatalysis; synergistic catalysis