October 24, 2000

Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4)

DCDominique CahardCentre National de la Recherche Scientifique CAChristophe AudouardCentre National de la Recherche Scientifique JPJean‐Christophe PlaqueventCentre National de la Recherche Scientifique

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Abstract

The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one-step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA-BF(4). This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.

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Cahard et al. (Tue,) studied this question.

synapsesocial.com/papers/69dcc2d2a5c75be4cfe53cfc https://doi.org/https://doi.org/10.1021/ol006610l

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