Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 32, Pages 10132-10135Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b06546
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Funding
- Astellas Foundation for Research on Metabolic Disorders
- MEXT
- AMED
- Grants-in-Aid for Scientific Research [26105751] Funding Source: KAKEN
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We report the first successful example of a highly enantioselective fluorolactonization with an electrophilic fluorinating reagent, Selectfluor (R), in the presence of a novel bifunctional organocatalyst. The catalyst design includes a carboxylate anion functioning as a phase-transfer agent and a benzyl alcohol unit to capture the substrate through hydrogen bonding. Fluorinated isobenzofuranones were obtained in good yields with up to 94% ee (97:3 er). On the basis of mechanistic studies, we propose a unique reaction mechanism with potential for further applications.
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