Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group

The Journal of Organic Chemistry
Tsutomu KonnoTakashi Ishihara

Abstract

The regioselective palladium-catalyzed formate reduction of gamma-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the gamma position, the corresponding reduction products with a fluoroalkyl group at the tertiary carbon being afforded in high yields. When the chiral allylic ester was employed, complete chirality transfer was observed, leading to the optically active materials in high yields.

Citations

Oct 23, 2008·Beilstein Journal of Organic Chemistry·Jun XuFeng-Ling Qing
Mar 16, 2017·Organic & Biomolecular Chemistry·Shin-Ichi IsobeMotoi Kawatsura
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