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Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations
http://hdl.handle.net/10069/00041722
http://hdl.handle.net/10069/00041722417cd2f0-885e-4eb6-b0cf-ace6b9ed7cae
名前 / ファイル | ライセンス | アクション |
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CPB70_599.pdf (905.5 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2022-09-13 | |||||
タイトル | ||||||
タイトル | Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | asymmetric catalysis | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | halogenation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | lactone | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | organocatalysis | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | selenium | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Nishiyori, Ryuichi
× Nishiyori, Ryuichi× Okuno, Ken× Chan, Bun× Shirakawa, Seiji |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | 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. |
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書誌情報 |
Chemical and Pharmaceutical Bulletin 巻 70, 号 9, p. 599-604, 発行日 2022-09-01 |
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出版者 | ||||||
出版者 | The Pharmaceutical Society of Japan | |||||
出版者別言語 | ||||||
公益社団法人 日本薬学会 | ||||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0009-2363 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1248/cpb.c22-00049 | |||||
権利 | ||||||
権利情報 | © 2022 The Pharmaceutical Society of Japan. | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Chemical & pharmaceutical bulletin, 70(9), pp. 599-604; 2022 |