New Fluorination Scheme | Chemical & Engineering News
Volume 90 Issue 1 | p. 24 | Concentrates
Issue Date: January 2, 2012

New Fluorination Scheme

Researchers develop charge-inverted approach to organofluorination
Department: Science & Technology
News Channels: Organic SCENE
Keywords: fluorination, chirality, enantioselectivity, catalysis

A common way to chirally fluorinate organic compounds is to use a technique called asymmetric phase-transfer catalysis with a chiral cation catalyst. Now, a team has made the charge-inverted version of that reaction—asymmetric phase-transfer catalysis with a chiral anion catalyst—a reality. In the reaction, the chiral anion catalyst uses anion exchange to shepherd a highly polar, cationic, solid fluorinating reagent into a nonpolar solvent, where the reagent induces a cyclization reaction that adds fluorine to alkene substrates in a highly enantio- and diastereoselective way. “The method generates heterocyclic products with two stereogenic centers, including a carbon-fluorine stereocenter that would be very difficult to construct “otherwise,” note the method’s developers, F. Dean Toste and coworkers at the University of California, Berkeley (Science, DOI: 10.1126/science.1213918). The “extremely powerful” reaction could provide “convenient access to a range of novel chiral fluorinated compounds with potential applications in biology, medicinal chemistry, and materials chemistry,” writes Mikiko Sodeoka of Japan’s RIKEN in a commentary about the work.

 
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