4.8 Article

Highly Regio- and Diastereoselective Synthesis of CF3-Substituted Lactones via Photoredox-Catalyzed Carbolactonization of Alkenoic Acids

Journal

ORGANIC LETTERS
Volume 16, Issue 3, Pages 780-783

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol403500y

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Funding

  1. Ministry of Education, Culture, Sports, Science of the Japanese Government [23750174]
  2. global COE program (the GCOE) Education and Research Center for Emergence of New Molecular Chemistry
  3. Grants-in-Aid for Scientific Research [14J10059, 26288045, 23750174, 22350026] Funding Source: KAKEN

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Trifluoromethylative lactonization of both terminal and internal alkenoic acids by photoredox catalysis has been developed. The use of a Ru photocatalyst and Umemoto's reagent as a CF3 source is key in the present carbolactonization. This is the first example of a highly endo- and diastereoselective synthesis of CF3-substituted five-, six-, and seven-membered ring lactones from internal alkenoic acids.

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