@article{oai:nagasaki-u.repo.nii.ac.jp:00027586, author = {Nishiyori, Ryuichi and Okuno, Ken and Chan, Bun and Shirakawa, Seiji}, issue = {9}, journal = {Chemical and Pharmaceutical Bulletin}, month = {Sep}, note = {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., Chemical & pharmaceutical bulletin, 70(9), pp. 599-604; 2022}, pages = {599--604}, title = {Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations}, volume = {70}, year = {2022} }