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Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines

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タイトル: Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines
著者: Murashige, Ryo 著作を一覧する
Hayashi, Yuka 著作を一覧する
Ohmori, Syo 著作を一覧する
Torii, Ayuko 著作を一覧する
Aizu, Yoko 著作を一覧する
Muto, Yasuyuki 著作を一覧する
Murai, Yuta 著作を一覧する
Oda, Yuji 著作を一覧する
Hashimoto, Makoto 著作を一覧する
キーワード: Friedel-Crafts acylation
Fries rearrangement
O-acylation
trifluoromethanesulfonic acid
homotyrosine
発行日: 2011年 1月21日
誌名: Tetrahedron
巻: 67
号: 3
開始ページ: 641
終了ページ: 649
出版社 DOI: 10.1016/j.tet.2010.11.047
抄録: Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.
資料タイプ: article (author version)
URI: http://hdl.handle.net/2115/44794
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 橋本 誠

 

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