title: Fluorine effects in organocatalysis - asymmetric Brønsted acid assisted Lewis base catalysis for the synthesis of trifluoromethylated heterocycles exploiting the negative hyperconjugation of the CF3-group.
abstract: An efficient Brønsted acid assisted Lewis base catalysis protocol for the synthesis of enantiomerically pure trifluoromethylated dihydropyridazines starting from readily available hydrazones and α,β-unsaturated aldehydes has been developed. The reaction exhibits high tolerance towards many functional groups and is applicable to various aliphatic, aromatic and hetero-aromatic α,β-unsaturated aldehydes, and provides the products in good yields and with excellent enantioselectivities.
authors.affiliation: RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany. magnus.rueping@rwth-aachen.de.
authors.forename: Chandra M R
authors.initials: CM
authors.lastname: Volla
authors.forename: Arindam
authors.initials: A
authors.lastname: Das
authors.forename: Iuliana
authors.initials: I
authors.lastname: Atodiresei
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006835:Hydrazones / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; D006835:Hydrazones; D058115:Lewis Bases; D005461:Fluorine