Synthesis of Chiral alpha-Fluoroketones through Catalytic Enantioselective Decarboxylation

摘要

A number of biologically active compounds bear secondary stereogenic centers next to a carbonyl group as a key structural feature,which are often susceptible to racemization during manipulation,storage,synthesis,or under physiological conditions under which they are expected to exhibit useful functions.Optically active alpha-fluoroketones could serve as nonracemizable surrogates of these compounds and have received much attention in medicinal chemistry.Interest in their synthesis therefore resulted in several recent reports on the enantioselective synthesis of alpha-fluorinated carbonyl compounds from the corresponding alpha-protio precursors,but the scope of the known fluorination methods is still limited.We report herein a new alternative synthetic strategy in which racemic alpha-fluoroketones are converted into optically active ketones through enantioselective C-C bond reorganization.