Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4)
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- 24 October 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (23) , 3699-3701
- https://doi.org/10.1021/ol006610l
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-BF4. 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.Keywords
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