Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids

• Hayama Noboru

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Azuma Takumi

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Kobayashi Yusuke

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Takemoto Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

抄録

The first intermolecular asymmetric Michael addition of nitrogen-nucleophiles to α,β-unsaturated carboxylic acids was achieved through a new type of arylboronic acid equipped with chiral aminothiourea. The use of BnONH₂ as a nucleophile gives a range of enantioenriched β-(benzyloxy)amino acid derivatives in good yields and with high enantioselectivity (up to 90% yield, 97% enantiomeric excess (ee)). The obtained products are efficiently converted to optically active β-amino acid and 1,2-diamine derivatives.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 64 (7), 704-717, 2016

  公益社団法人 日本薬学会

キーワード

• aza-Michael addition
• α,β-unsaturated carboxylic acid
• integrated catalyst
• thiourea
• arylboronic acid
• <i>O</i>-benzylhydroxylamine

詳細情報

• CRID: 1390282679155783552
• NII論文ID: 130005160066
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c15-00983
• ISSN: 13475223
• ISSN: 00092363
• HANDLE: 2433/235952
• NDL書誌ID: 027451391
• PubMed: 27373626
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I027451391
• Web Site: https://www.jstage.jst.go.jp/article/cpb/64/7/64_c15-00983/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2017038253
• 本文言語コード: en
• データソース種別:
  • JaLC
  • IRDB
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可