Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 6, Pages 1738-1741Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja111163u
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Funding
- NIHGMS [R01 GM078201-01-01]
- NSERC
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The first highly enantioselective alpha-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone alpha-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric a-fluorination of a variety of carbo- and heterocyclic substrates. Furthermore, this protocol also provides diastereo-, regio-, and chemoselective catalyst control in fluorinations involving complex carbonyl systems.
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