title: Bidentate Lewis Acid Catalyzed Domino Diels-Alder Reaction of Phthalazine for the Synthesis of Bridged Oligocyclic Tetrahydronaphthalenes.
abstract: A domino process consisting of an inverse and a normal electron-demand Diels-Alder reaction is presented for the formation of bridged tri- and tetracyclic 1,2,3,4-tetrahydronaphthalenes catalyzed by a bidentate Lewis acid. The products were synthesized in a one-pot reaction from commercially available starting materials and contain up to six stereogenic centers. The tetrahydronaphthalenes were isolated as single diastereomers and are derivatives of phenylethylamine, which is well-known as a scaffold of amphetamine or dopamine.
authors.affiliation: Institute of Organic Chemistry, Justus Liebig University Giessen , Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
authors.forename: Luca
authors.initials: L
authors.lastname: Schweighauser
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors.forename: Ina
authors.initials: I
authors.lastname: Bodoky
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors.forename: Simon N
authors.initials: SN
authors.lastname: Kessler
authors.affiliation: Department of Chemistry, University of Basel , St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors.forename: Daniel
authors.initials: D
authors.lastname: Häussinger
authors.affiliation: Fachbereich Chemie and Wissenschaftliches Zentrum für Materialwissenschaften (WZMW), Philipps-Universität Marburg , Hans-Meerwein-Strasse, 35043 Marburg, Germany.
authors.forename: Carsten
authors.initials: C
authors.lastname: Donsbach
authors.affiliation: Institute of Organic Chemistry, Justus Liebig University Giessen , Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
authors.forename: Hermann A
authors.initials: HA
authors.lastname: Wegner
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D010793:Phthalazines / Q000737:chemistry*; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006572:Heterocyclic Compounds, Bridged-Ring; D058116:Lewis Acids; D010793:Phthalazines; D013764:Tetrahydronaphthalenes; C043388:phthalazine