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

• Murashige, Ryo

• Hayashi, Yuka

• Ohmori, Syo

• Torii, Ayuko

• Aizu, Yoko

• Muto, Yasuyuki

• Murai, Yuta

• Oda, Yuji

• Hashimoto, Makoto

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.

収録刊行物

• Tetrahedron

  Tetrahedron 67 (3), 641-649, 2011-01-21

  Elsevier BV

キーワード

• Friedel-Crafts acylation
• Fries rearrangement
• O-acylation
• trifluoromethanesulfonic acid
• homotyrosine

詳細情報

• CRID: 1050282813983890176
• NII論文ID: 120002741676
• NII書誌ID: AA00861787
• DOI: 10.1016/j.tet.2010.11.047
• HANDLE: 2115/44794
• ISSN: 00404020
• Web Site: https://api.elsevier.com/content/article/PII:S0040402010016923?httpAccept=text/xml
• Web Site: https://api.elsevier.com/content/article/PII:S0040402010016923?httpAccept=text/plain
• 本文言語コード: en
• 資料種別: journal article
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