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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概要
- 論文の詳細を見る
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.
- 2011-01-21
著者
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橋本 誠
北海道大学大学院農学研究院
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Hashimoto Makoto
Obihiro Univ. Agriculture And Veterinary Medicine Hokkaido Jpn
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Hashidoko Yasuyuki
Graduate School And Res. Fac. Of Agriculture Hokkaido Univ.
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Hashidoko Yasuyuki
Division Of Applied Science Graduate School Of Agriculture Hokkaido University
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Hashimoto Makoto
Div. Of Applied Sci. Graduate School Of Agriculture Hokkaido Univ.
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MURAI Yuta
Division of Applied Science, Graduate School of Agriculture, Hokkaido University
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Hashimoto Makoto
Department Of Agricultural And Life Science Obihiro University Of Agriculture And Veterinary Medicin
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Hashimoto Makoto
Department Of Agricultural And Life Science Obihiro University Of Agriculture And Veterinary Medicin
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Hashimoto Makoto
Department Of Bioresource Science Obihiro University Agriculture
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Hashimoto Makoto
Department Of Biology And Biochemistry University Of Bath:department Of Bioresource Science Obihiro
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Hashimoto Makoto
Department Of Agricultural And Life Science Obihiro University Of Agriculture And Veterinary Medicin
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Murai Yuta
Div. Of Applied Sci. Graduate School Of Agriculture Hokkaido Univ.
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