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Asymmetric Electrophilic Fluorination Using an Anionic Chiral Phase-Transfer Catalyst
Ist Teil von
Science (American Association for the Advancement of Science), 2011-12, Vol.334 (6063), p.1681-1684
Ort / Verlag
Washington, DC: American Association for the Advancement of Science
Erscheinungsjahr
2011
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. Here, we present evidence that a largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is applied to the enantioselective fluorocyclization of olefins with a cationic fluorinating agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity, especially considering the scarcity of alternative approaches. This technology can in principle be applied to the large portion of reaction space that uses positively charged reagents and reaction intermediates.