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
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- Okuno Ken
- Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University
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- Chan Bun
- Graduate School of Engineering, Nagasaki University
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- Shirakawa Seiji
- Department of Environmental Science, Graduate School of Fisheries and Environmental Sciences, Nagasaki University
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説明
<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>
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 70 (9), 599-604, 2022-09-01
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390856218602244224
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- ISSN
- 13475223
- 00092363
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- HANDLE
- 10069/00041722
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- PubMed
- 36047230
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- JaLC
- IRDB
- Crossref
- PubMed
- KAKEN
- OpenAIRE
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