title: Synthesis with perfect atom economy: generation of furan derivatives by 1,3-dipolar cycloaddition of acetylenedicarboxylates at cyclooctynes.
abstract: Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b-d, orthoesters 4a-c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy.
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. klaus.banert@chemie.tu-chemnitz.de.
authors.forename: Klaus
authors.initials: K
authors.lastname: Banert
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. sandra.bochmann@chemie.tu-chemnitz.de.
authors.forename: Sandra
authors.initials: S
authors.lastname: Bochmann
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. andreas.ihle@chemie.tu-chemnitz.de.
authors.forename: Andreas
authors.initials: A
authors.lastname: Ihle
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. oliver.plefka@web.de.
authors.forename: Oliver
authors.initials: O
authors.lastname: Plefka
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. florian.taubert@s2008.tu-chemnitz.de.
authors.forename: Florian
authors.initials: F
authors.lastname: Taubert
authors.affiliation: Organic Chemistry, Technische Universität Chemnitz, Strasse der Nationen 62, 09111 Chemnitz, Germany. tina.walther@s2008.tu-chemnitz.de.
authors.forename: Tina
authors.initials: T
authors.lastname: Walther
authors.affiliation: Inorganic Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany. marcus.korb@s2007.tu-chemnitz.de.
authors.forename: Marcus
authors.initials: M
authors.lastname: Korb
authors.affiliation: Inorganic Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany. tobias.rueffer@chemie.tu-chemnitz.de.
authors.forename: Tobias
authors.initials: T
authors.lastname: Rüffer
authors.affiliation: Inorganic Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany. heinrich.lang@chemie.tu-chemnitz.de.
authors.forename: Heinrich
authors.initials: H
authors.lastname: Lang
mesh_terms: D061565:Cycloaddition Reaction; D034242:Cyclooctanes / Q000737:chemistry; D003998:Dicarboxylic Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*
chemical_list: D034242:Cyclooctanes; D003998:Dicarboxylic Acids; D004852:Epoxy Compounds; D005663:Furans