Enantioselective organocatalytic α-fluorination of cyclic ketones.
The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-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 α-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.
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
Piotr
P
Kwiatkowski
Teresa D
TD
Beeson
Jay C
JC
Conrad
David W C
DW
MacMillan
D002384:Catalysis; D054879:Halogenation; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007659:Ketones
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