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カルコゲン官能基を有するα,β-不飽和カルボニル化合物と求電子剤の連結反応
https://gifu-pu.repo.nii.ac.jp/records/12802
https://gifu-pu.repo.nii.ac.jp/records/12802057a4ea5-30af-4211-8177-983795d12349
名前 / ファイル | ライセンス | アクション |
---|---|---|
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Item type | 紀要論文(ELS) / Departmental Bulletin Paper(1) | |||||
---|---|---|---|---|---|---|
公開日 | 2006-06-30 | |||||
タイトル | ||||||
タイトル | カルコゲン官能基を有するα,β-不飽和カルボニル化合物と求電子剤の連結反応 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | One-pot Coupling of α, β-Unsaturated Carbonyl Compounds Bearing a Chalcogen Group and Electrophiles Using a Lewis Acid | |||||
言語 | ||||||
言語 | jpn | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | 連続反応 | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | マイケルーアルドール反応 | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | 電子不足アルケン | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | 求電子剤 | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | 不斉合成 | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Morita-Baylis-Hillman型付加物 | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | tandem reaction | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Michael-aldol reaction | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | electron deficient alkene | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | electrophile | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | asymmetric synthesis | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | Morita-Baylis-Hillman adduct | |||||
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 | departmental bulletin paper | |||||
ページ属性 | ||||||
内容記述タイプ | Other | |||||
内容記述 | P(論文) | |||||
記事種別(日) | ||||||
値 | 総説 | |||||
記事種別(英) | ||||||
言語 | en | |||||
値 | Review | |||||
著者名(日) |
片岡, 貞
× 片岡, 貞 |
|||||
著者名よみ |
カタオカ, タダシ
× カタオカ, タダシ |
|||||
著者名(英) |
KATAOKA, Tadashi
× KATAOKA, Tadashi |
|||||
著者所属(日) | ||||||
値 | 岐阜薬科大学薬化学教室 | |||||
著者所属(英) | ||||||
言語 | en | |||||
値 | Laboratory of Pharmaceutical Chemistry, Gifu Pharmaceutical University | |||||
抄録(日) | ||||||
内容記述タイプ | Other | |||||
内容記述 | 分子内にカルコゲニド、チオアミドなどの官能基とエノン残基をもつ化合物がルイス酸によって閉環し、同時に発生したエノラートイオンが求電子剤と反応する新しい型の連続マイケルーアルドール反応を開発した。1-[2-(Methylchalcogeno)phenyl]propenoneとアルデヒドの反応はBF_3・Et_2O存在下進行し、反応混合物をEt_3Nで後処理すると、Morita-Baylis-Hillman型付加物を好収率で与えた。本反応では求電子剤としてケトン、α-ジケトン、α-オキソエステルなども反応した。3-Cinnamoyl-1,3-oxazolidine-2-thioneとアルデヒドとの反応からは、4つのヘテロ原子と結合した橋頭位炭素をもつ三環系化合物が得られた。この反応に光学活性チオンを用いると、4つの不斉点が一挙に構築された。三環系生成物は加水分解、S-メチル化後、NaBH_4で還元して、不斉点が3つ連続した1,3-ジオールに誘導した。 | |||||
抄録(英) | ||||||
内容記述タイプ | Other | |||||
内容記述 | A new tandem Michael-aldol reaction of enones bearing a chalcogenide or a thioamide group with electrophiles was developed. Reactions of 1-[2-(methylchalcogeno)phenyl]propenones with electrophiles gave α-(α-hydroxyalkyl)enones (Morita-Baylis-Hillman adducts) after the work-up of the reaction mixture with Et_3N. Electrophiles not only aldehydes but also α-diketones and α-keto esters were reactive to the reactions. Tricyclic compounds with a bridgehead bound to four heteroatoms were obtained from the reactions of 3-cinnamoyl-1,3-oxazolidine-2-thiones with aldehydes. Four stereocenters were simultaneously formed when an optically active thione was used. Tricyclic products were led to 1,3-diols bearing three consecutive stereocenters using acid hydrolysis, S-methylation and reductive removal of the chiral auxiliary. | |||||
雑誌書誌ID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AN00053514 | |||||
書誌情報 |
岐阜藥科大學紀要 en : The annual proceedings of Gifu College of Pharmacy 巻 55, p. 1-17, 発行日 2006-06-30 |