title: Asymmetric Catalytic Aza-Diels-Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis.
abstract: An asymmetric catalytic aza-Diels-Alder/ring-closing cascade reaction between acylhydrazones and in situ formed trienamines is presented. The reaction proceeds through a formal aza-Diels-Alder cycloaddition, followed by a ring-closing reaction forming the hemiaminal ring leading to chiral bicyclic azaheterocycles in moderate to good yield (up to 71 %), good enantio- (up to 92 % ee) and diastereoselectivity (up to >20:1 d.r.). Furthermore, transformations are presented to show the potential application of the formed product.
authors: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors: Yang
authors: Y
authors: Li
authors: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors: Casper
authors: C
authors: Barløse
authors: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors: Julie
authors: J
authors: Jørgensen
authors: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors: Bjørn Dreiø
authors: BD
authors: Carlsen
authors: Department of Chemistry, Aarhus University, 8000, Aarhus C, Denmark.
authors: Karl Anker
authors: KA
authors: Jørgensen
keywords: asymmetric catalysis; cycloaddition; heterocycles; organocatalysis; synthetic methods