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

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 et al.

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

Permalink : https://hdl.handle.net/2115/44794

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アクセス権	open access
URI	https://hdl.handle.net/2115/44794
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 ; Hayashi, Yuka ; Ohmori, Syo ; Torii, Ayuko ; Aizu, Yoko ; Muto, Yasuyuki ; Murai, Yuta ; Oda, Yuji ; Hashimoto, Makoto
著者名 Murashige, Ryo
著者名 Hayashi, Yuka
著者名 Ohmori, Syo
著者名 Torii, Ayuko
著者名 Aizu, Yoko
著者名 Muto, Yasuyuki
著者名 Murai, Yuta
著者名 Oda, Yuji
著者名 Hashimoto, Makoto
言語	英語
キーワード	Friedel-Crafts acylation
	Fries rearrangement
	O-acylation
	trifluoromethanesulfonic acid
	homotyrosine
発行日	2011-01-21
収録物名	Tetrahedron
巻(号)	67(3)
ページ	641-649
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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	0040-4020
NCID	AA00861787
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.tet.2010.11.047