Asymmetric Synthesis of α‐Amino Phosphonic Acids using Stable Imino Phosphonate as a Universal Precursor

• Inokuma, Tsubasa

• Sakakibara, Takuya

• Someno, Takatoshi

• Masui, Kana

• Shigenaga, Akira

• Otaka, Akira

• Yamada, Ken-ichi

抄録

A practical method for synthesizing chiral α-amino phosphonic acid derivatives was developed. Readily available and stable N-o-nitrophenylsulfenyl (Nps) imino phosphonate was utilized as a substrate for a highly enantioselective Friedel–Crafts-type addition of indole or pyrrole nucleophiles catalyzed by chiral phosphoric acid. The resulting adduct was easily converted to N-9-fluorenylmethyloxycarbonyl (Fmoc) amino phosphonic acid, which is useful for synthesizing peptides containing an amino phosphonic acid.

収録刊行物

• Chemistry- A European Journal

  Chemistry- A European Journal 25 (60), 13829-13832, 2019-08-26

  Wiley-VCH

キーワード

• amino phosphonic acid
• asymmetric catalysis
• Friedel–Crafts–type reaction
• imino phosphonate
• organocatalysis

詳細情報

• CRID: 1050004225345584512
• NII論文ID: 120006886354
• NII書誌ID: AA11076269
• ISSN: 15213765
• ISSN: 09476539
• DOI: 10.1002/chem.201903572
• Web Site: http://repo.lib.tokushima-u.ac.jp/115143
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201903572
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201903572
• 本文言語コード: en
• 資料種別: journal article
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