Molecular Transformation Based on an Innovative Catalytic System

• Takemoto Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

抄録

Novel innovative catalytic systems such as hydrogen-bond donors and thiourea hybrid catalysts have been developed for the asymmetric synthesis of biologically important pharmaceuticals and natural products. Benzothiadiazines possess a stronger hydrogen-bond donor ability compared to thioureas and exhibit remarkable catalytic performance for the activation of α,β-unsaturated amides. Hybrid thioureas (bearing an arylboronic acid and an ammonium salt) efficiently promote the hetero-Michael addition to α,β-unsaturated carboxylic acids and the O-alkylation of keto enols with 5-chlorofuran-2(5H)-one. These hybrid catalysts enable the first total synthesis of non-racemic avenaol, a noncanonical strigolactone, as well as the asymmetric synthesis of several pharmaceuticals. In addition, this study discovers unique chemical phenomena (i.e., the dual role of benzoic acid as a boron ligand and a proton shuttle, the chirality switch of products by solvent used, and the dynamic kinetic resolution of a racemic electrophile in an S_N2-type reaction).

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 69 (9), 819-831, 2021-09-01

  公益社団法人 日本薬学会

キーワード

• catalysis
• chirality switch
• thiourea
• arylboronic acid
• ammonium salt
• avenaol

詳細情報

• CRID: 1390289232189184512
• NII論文ID: 130008081982
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c21-00390
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 031643068
• PubMed: 34470946
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I031643068
• Web Site: https://www.jstage.jst.go.jp/article/cpb/69/9/69_c21-00390/_pdf
• 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