Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations

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  • Nishiyori Ryuichi
    Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University
  • Okuno Ken
    Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University
  • Chan Bun
    Graduate School of Engineering, Nagasaki University
  • Shirakawa Seiji
    Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University

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<p>1,1′-Bi-2-naphthol (BINOL)-derived chiral bifunctional sulfide and selenide catalysts that possess a hydroxy group are known to be effective catalysts for enantioselective bromolactonizations. When applied to asymmetric iodolactonizations of 4-pentenoic acids, these catalysts yield chiral γ-butyrolactone products that are important compounds in medicinal chemistry. Although chiral bifunctional selenides have shown good catalytic performances in enantioselective iodolactonizations, reactions with BINOL-derived chiral sulfide catalysts unexpectedly gave iodolactonization products in nearly racemic forms. The roles of chalcogenide moieties and hydroxy groups on bifunctional catalysts were investigated, and the importance of both a selenide moiety and a hydroxy group on chiral bifunctional selenide catalysts to achieve enantioselective iodolactonizations was clarified. An optimized chiral bifunctional selenide catalyst was applied to the asymmetric synthesis of chiral γ-butyrolactones and phthalides. Furthermore, the utility of chiral bifunctional selenides was also demonstrated in the catalytic enantioselective desymmetrizing iodolactonization of α,α-diallyl carboxylic acids.</p>

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