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Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Agriculture / Faculty of Agriculture >
Peer-reviewed Journal Articles, etc >
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
| 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)
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Submitter: 橋本 誠
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