title: 1,4-Naphthoquinones in H-bond-directed trienamine-mediated strategies.
abstract: The synthesis of optically active, carboannulated dihydronaphthoquinone and naphthoquinone derivatives with up to four stereogenic centers is demonstrated by H-bond-directed, trienamine-mediated [4 + 2]-cycloadditions. The outcome of the reaction between 2,4-dienals and 1,4-naphthoquinones is controlled by the substituent in the 2-position of the 1,4-naphthoquinone. In the case of sterically demanding 2-substituted derivatives, dihydronaphthoquinones are obtained. However, when a hydrogen atom is present in the 2-position, a subsequent oxidation of the initially formed cycloadducts occurs yielding naphthoquinones.
authors.affiliation: Center for Catalysis, Department of Chemistry, Aarhus University , 8000 Aarhus C, Denmark.
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Albrecht
authors.forename: Clarisa Villegas
authors.initials: CV
authors.lastname: Gómez
authors.forename: Christian Borch
authors.initials: CB
authors.lastname: Jacobsen
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D009285:Naphthoquinones; C035342:1,4-naphthoquinone