Asymmetric Bis(alkoxycarbonylation) Reaction of Cyclic Olefins Catalyzed by Palladium in the Presence of Copper(I) Triflate

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  • Takahiro Aratani
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Kenji Tahara
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Susumu Takeuchi
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Satoko Kitamura
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Moemi Murai
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Shuhei Fujinami
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Katsuhiko Inomata
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
  • Yutaka Ukaji
    Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University

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<jats:title>Abstract</jats:title> <jats:p>A palladium-catalyzed asymmetric bis(alkoxycarbonylation) reaction of 1,2-dihydronaphthalenes and related cyclic olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand under normal pressure of carbon monoxide and oxygen to give the corresponding optically active cis-dicarboxylates with enantioselectivities up to 94% ee. An asymmetric intra- and intermolecular bis(alkoxycarbonylation) reaction of a prochiral diol possessing dihydronaphthalene skeleton also proceeded enantioselectively by an appropriate selection of the substituent of bioxazoline ligand. The carbonylation product derived from 8-methoxy-1,2-dihydronaphthalene was applied to the synthesis of a biologically active hexahydrobenz[e]isoindole derivative.</jats:p>

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