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Construction of Terminal Conjugated Enynes: Cu-Mediated Cross-Coupling Reaction of Alkenyldialkylborane with (Trimethylsilyl)ethynyl Bromide
https://kitami-it.repo.nii.ac.jp/records/7172
https://kitami-it.repo.nii.ac.jp/records/7172fba1c397-22c7-43a5-acfa-00d2ebf56967
名前 / ファイル | ライセンス | アクション |
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2007-05-11 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Construction of Terminal Conjugated Enynes: Cu-Mediated Cross-Coupling Reaction of Alkenyldialkylborane with (Trimethylsilyl)ethynyl Bromide | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | journal article | |||||
アクセス権 | ||||||
アクセス権 | open access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
著者 |
Hoshi, Masayuki
× Hoshi, Masayuki× Kawamura, Noritsugu× Shirakawa, Kazuya |
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著者別名 | ||||||
姓名 | 星, 雅之 | |||||
言語 | ja | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | The cross-coupling reaction of (E)- and (Z)-alk-1-enyldialkylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a catalytic amount of Cu(acac)_2 and a base under extremely mild conditions to provide conjugated enynes whose carbon-carbon triple bond is distal position. The use of 1M NaOMe as the base results in not only cross-coupling but also desilylation affording both (E)- and (Z)-alk-3-en-1-ynes exclusively, while the use of LiOH・H_2O instead of 1M NaOMe preferentially gives both (E)- and (Z)-1-(trimethylsilyl)alk-3-en-1-ynes with high regio- and stereoselectivity. On the other hand, the cross-coupling reaction of (Z)-1-(trimethylsilyl)alk-1-enyldicyclohexylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a small amount of CuI and aqueous NaOH under extremely mild conditions to afford (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-yne with high regio- and stereoselectivity. In addition, treatment of the resultant product with 1M NaOMe leads to the stereoselective formation of (Z)-3-(trimethylsilyl)alk-3-en-1-yne in a one-pot manner. | |||||
書誌情報 |
Synlett 巻 2006, 号 12, p. 1961-1970, 発行日 2006-06 |
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DOI | ||||||
識別子タイプ | DOI | |||||
関連識別子 | http://doi.org/10.1055/s-2006-942373 | |||||
権利 | ||||||
権利情報 | http://www.thieme-connect.de/ejournals/abstract/synthesis/doi/10.1055/s-2006-942373 | |||||
権利 | ||||||
権利情報 | Georg Thieme Verlag, M.Hoshi, K.Shirakawa, Synlett, 2006(12), 2006, 1961-1970. c 2006 Georg Thieme Verlag KG. | |||||
フォーマット | ||||||
内容記述タイプ | Other | |||||
内容記述 | application/pdf | |||||
出版者 | ||||||
出版者 | Georg Thieme Verlag | |||||
著者版フラグ | ||||||
値 | author | |||||
出版タイプ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa |