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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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Title: 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
Authors: Murashige, Ryo Browse this author
Hayashi, Yuka Browse this author
Ohmori, Syo Browse this author
Torii, Ayuko Browse this author
Aizu, Yoko Browse this author
Muto, Yasuyuki Browse this author
Murai, Yuta Browse this author
Oda, Yuji Browse this author
Hashimoto, Makoto Browse this author
Keywords: Friedel-Crafts acylation
Fries rearrangement
O-acylation
trifluoromethanesulfonic acid
homotyrosine
Issue Date: 21-Jan-2011
Journal Title: Tetrahedron
Volume: 67
Issue: 3
Start Page: 641
End Page: 649
Publisher DOI: 10.1016/j.tet.2010.11.047
Abstract: 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.
Type: article (author version)
URI: http://hdl.handle.net/2115/44794
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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