Item type |
学術雑誌論文 / Journal Article(1) |
公開日 |
2010-10-26 |
タイトル |
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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 |
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言語 |
eng |
DOI |
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関連識別子 |
https://doi.org/10.1016/j.tet.2010.01.095 |
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関連名称 |
10.1016/j.tet.2010.01.095 |
キーワード |
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主題 |
1,3-Dipolar cycloaddition, Carbonyl ylide, Chiral Lewis acid, Asymmetric synthesis, Metal catalyst, Diazocarbonyl compound |
資源タイプ |
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資源 |
http://purl.org/coar/resource_type/c_6501 |
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タイプ |
journal article |
著者 |
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 |
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氏名 |
Suga, Hiroyuki |
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URL |
http://soar-rd.shinshu-u.ac.jp/profile/ja.HmShyVfp.html |
出版者 |
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出版者 |
PERGAMON-ELSEVIER SCIENCE LTD |
引用 |
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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 |
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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) |
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内容記述 |
Article |
ISSN |
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収録物識別子タイプ |
ISSN |
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収録物識別子 |
0040-4020 |
書誌レコードID |
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収録物識別子タイプ |
NCID |
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収録物識別子 |
AA11539786 |
権利 |
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権利情報 |
Copyright (c) 2010 Elsevier Ltd. |
出版タイプ |
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出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
WoS |
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URL |
http://gateway.isiknowledge.com/gateway/Gateway.cgi?&GWVersion=2&SrcAuth=ShinshuUniv&SrcApp=ShinshuUniv&DestLinkType=FullRecord&DestApp=WOS&KeyUT=000276588400022 |