Catalytic asymmetric synthesis of tertiary alkyl fluorides: Negishi cross-couplings of racemic ?,?-dihaloketones.

ABSTRACT: The development of new approaches to the construction of fluorine-containing target molecules is important for a variety of scientific disciplines, including medicinal chemistry. In this Article, we describe a method for the catalytic enantioselective synthesis of tertiary alkyl fluorides through Negishi reactions of racemic ?-halo-?-fluoroketones, which represents the first catalytic asymmetric cross-coupling that employs geminal dihalides as electrophiles. Thus, selective reaction of a C-Br (or C-Cl) bond in the presence of a C-F bond can be achieved with the aid of a nickel/bis(oxazoline) catalyst. The products of the stereoconvergent cross-couplings, enantioenriched tertiary ?-fluoroketones, can be converted into an array of interesting organofluorine compounds.

SUBMITTER: Liang Y 

PROVIDER: S-EPMC4004247 | biostudies-other | 2014 Apr

REPOSITORIES: biostudies-other