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The reactions were effectively catalyzed by Eu(OTf)(3), Ho(OTf)(3), or Gd(OTf)(3) complexes (10 mol %) of chiral 2,6-bis[(4S,5S)-4,5-diphenyl-2-oxazolinyl]pyridine. The reactions with the other electron-rich dipolarophiles such as ally! alcohol, 2,3-dihydrofuran, and butyl-tert-butyldimethylsilylketene acetal showed moderate enanantioselectivities (60-73% ee). Good to high enantioselectivities (73-97% ee) were also obtained for the cycloadditions between 3-acyl-2-benzopyrylium-4-olates, generated from methyl 2-(2-diazo-1,3-dioxoalkyl)benzoates and butyl or cyclohexyl vinyl ethers, in the presence of binaphthyldiimine (BINIM)-Ni(II) complexes (10 mol %). Under similar conditions, the reaction between methyl 2-(2-diazo-1,3-dioxohexyl)benzoate and 2,3-dihydrofuran was highly endo-selective, and moderately enantioselective (70% ee). For the BINIM-Ni(II)-catalyzed reactions of cyclohexyl vinyl ether, the use of an epoxyindanone as the 3-acyl-2-benzopyrylium-4-olate precursor revealed that the chiral Lewis acid can function as a catalyst for asymmetric induction. The scope of the cyclic carbonyl ylides was extended to those generated from 1-diazo-2,5-pentanedione derivatives, which were reacted with butyl or TBS vinyl ether and catalyzed using the (4S,5S)-Pybox-4,5-Ph-2-Lu(OTf)(3) complex to give good levels of asymmetric inductions (75-84% ee). (C) 2010 Elsevier Ltd. 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Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates
http://hdl.handle.net/10091/10736
http://hdl.handle.net/10091/10736a428fc5e-f992-47ae-ab87-ea37f0631245
名前 / ファイル | ライセンス | アクション |
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Inverse_Electron_Demand_Asymmetric_Cycloadditions.pdf (1.4 MB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2010-10-26 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids-Scope and limitations of diazo and olefinic substrates | |||||
言語 | ||||||
言語 | eng | |||||
DOI | ||||||
識別子タイプ | DOI | |||||
関連識別子 | https://doi.org/10.1016/j.tet.2010.01.095 | |||||
関連名称 | 10.1016/j.tet.2010.01.095 | |||||
キーワード | ||||||
主題 | 1,3-Dipolar cycloaddition, Carbonyl ylide, Chiral Lewis acid, Asymmetric synthesis, Metal catalyst, Diazocarbonyl compound | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | journal article | |||||
著者 |
Suga, Hiroyuki
× Suga, Hiroyuki× Higuchi, Satoshi× Ohtsuka, Motoo× Ishimoto, Daisuke× Arikawa, Tadashi× Hashimoto, Yuta× Misawa, Shunta× Tsuchida, Teruko× Kakehi, Akikazu× Baba, Toshihide |
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信州大学研究者総覧へのリンク | ||||||
氏名 | Suga, Hiroyuki | |||||
URL | http://soar-rd.shinshu-u.ac.jp/profile/ja.HmShyVfp.html | |||||
出版者 | ||||||
出版者 | PERGAMON-ELSEVIER SCIENCE LTD | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Tetrahedron. 66(16):3070-3089 (2010) | |||||
書誌情報 |
Tetrahedron 巻 66, 号 16, p. 3070-3089, 発行日 2010-04-17 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | High enantioselectivities (94–96% ee) were obtained for the inverse electron-demand 1,3-dipolar cycloadditions between cyclohexyl vinyl ether and 2-benzopyrylium-4-olate generated via Rh₂(OAc)₄-catalyzed decomposition of o-methoxycarbonyl-α-diazoacetophenone. The reactions were effectively catalyzed by Eu(OTf)₃, Ho(OTf)₃, or Gd(OTf)₃ complexes (10 mol %) of chiral 2,6-bis[(4S,5S)-4,5-diphenyl-2-oxazolinyl]pyridine. The reactions with the other electron-rich dipolarophiles such as allyl alcohol, 2,3-dihydrofuran, and butyl-tert-butyldimethylsilylketene acetal showed moderate enanantioselectivities (60–73% ee). Good to high enantioselectivities (73–97% ee) were also obtained for the cycloadditions between 3-acyl-2-benzopyrylium-4-olates, generated from methyl 2-(2-diazo-1,3-dioxoalkyl)benzoates and butyl or cyclohexyl vinyl ethers, in the presence of binaphthyldiimine (BINIM)–Ni(II) complexes (10 mol %). Under similar conditions, the reaction between methyl 2-(2-diazo-1,3-dioxohexyl)benzoate and 2,3-dihydrofuran was highly endo-selective, and moderately enantioselective (70% ee). For the BINIM–Ni(II)-catalyzed reactions of cyclohexyl vinyl ether, the use of an epoxyindanone as the 3-acyl-2-benzopyrylium-4-olate precursor revealed that the chiral Lewis acid can function as a catalyst for asymmetric induction. The scope of the cyclic carbonyl ylides was extended to those generated from 1-diazo-2,5-pentanedione derivatives, which were reacted with butyl or TBS vinyl ether and catalyzed using the (4S,5S)-Pybox-4,5-Ph₂–Lu(OTf)₃ complex to give good levels of asymmetric inductions (75–84% ee). | |||||
資源タイプ(コンテンツの種類) | ||||||
内容記述タイプ | Other | |||||
内容記述 | Article | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0040-4020 | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA11539786 | |||||
権利 | ||||||
権利情報 | Copyright (c) 2010 Elsevier Ltd. | |||||
出版タイプ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
WoS | ||||||
表示名 | Web of Science | |||||
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