title: Biology-oriented synthesis of benzopyrano[3,4-c]pyrrolidines.
abstract: A natural product inspired synthesis of 6,6,5-tricyclic compounds via a silver(I)-catalyzed formal 1,3-dipolar cycloaddition of coumarins with α-iminoesters was developed. The reaction proceeds in a stepwise reaction course under formation of the trans-substituted diastereomer with respect to the 1,3-dipole and shows a broad substrate scope.
authors: Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany; Chemical Biology, Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany.
authors: Marco
authors: M
authors: Potowski
authors: Inorganic Chemistry, Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany.
authors: Christopher
authors: C
authors: Golz
authors: Inorganic Chemistry, Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany.
authors: Carsten
authors: C
authors: Strohmann
authors: Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany; Chemical Biology, Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany. Electronic address: andrey.antonchick@mpi-dortmund.mpg.de.
authors: Andrey P
authors: AP
authors: Antonchick
authors: Department of Chemical Biology, Max-Planck-Institute of Molecular Physiology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany; Chemical Biology, Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany. Electronic address: herbert.waldmann@mpi-dortmund.mpg.de.
authors: Herbert
authors: H
authors: Waldmann
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D061565:Cycloaddition Reaction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001391:Azo Compounds; D001578:Benzopyrans; D003374:Coumarins; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; D012834:Silver; C030123:coumarin
keywords: Azomethine ylide; Biology-oriented synthesis (BIOS); Catalysis; Coumarin; [2+3] cycloaddition