Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

• Ishizawa Kouhei

  Graduate School of Pharmaceutical Sciences, The University of Tokyo Sohyaku Innovative Research Division, Mitsubishi Tanabe Pharma Corporation

• Nagai Hideoki

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

• Shimizu Yohei

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

• Kanai Motomu

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

抄録

A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the α-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 66 (3), 231-234, 2018

  公益社団法人 日本薬学会

キーワード

• carboxylic acid
• aldol reaction
• boron catalyst
• trifluoromethyl ketone

詳細情報

• CRID: 1390282679155294080
• NII論文ID: 130006407099
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c17-00545
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 028853948
• PubMed: 28824027
• Web Site: http://id.ndl.go.jp/bib/028853948
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I028853948
• Web Site: https://www.jstage.jst.go.jp/article/cpb/66/3/66_c17-00545/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2019023871
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可