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Enantioselective organocatalytic ?-fluorination of cyclic ketones.

ABSTRACT: The first highly enantioselective ?-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone ?-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 ?-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.

SUBMITTER: Kwiatkowski P

PROVIDER: S-EPMC3107934 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Enantioselective organocatalytic α-fluorination of cyclic ketones.

Kwiatkowski Piotr P Beeson Teresa D TD Conrad Jay C JC MacMillan David W C DW

Journal of the American Chemical Society 20110119 6

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 diaster ...[more]

PMID: 21247133

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