Enantioselective organocatalytic α-fluorination of cyclic ketones.

ABSTRACT: 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.

SUBMITTER: Kwiatkowski P 

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

REPOSITORIES: biostudies-literature