Organocatalytic Synthesis of Chiral Halogenated Compounds

This account summarizes our recent efforts in the enantioselective organocatalytic synthesis of chiral halogenated compounds. The enantioselective alpha-halogenation of aldehydes, decarboxylative chlorination of beta-keto acids, and enantioselective C-C bond formation at the trifluoromethylated prochiral carbon to yield the corresponding organohalides with chlorinated, fluorinated, or trifluoromethylated chiral stereogenic centers are discussed. We applied common organocatalysts, such as Jorgensen-Hayashi catalyst and cinchona alkaloid-derivatived catalyst, and developed novel chiral amine catalysts for these reactions. This account also discusses stereospecific derivatizations of the resulting chiral halogenated compounds via nucleophilic substitution. Thus, we synthesized many novel chiral compounds that have not been reported, even as racemates.

Automated summary

This paper summarizes our recent efforts in the enantioselective organocatalytic synthesis of chiral halogenated compounds. The discussion includes enantioselective alpha-halogenation of aldehydes, decarboxylative chlorination of beta-keto acids, and enantioselective C-C bond formation at the trifluoromethylated prochiral carbon to yield organohalides with chlorinated, fluorinated, or trifluoromethylated chiral stereogenic centers. Common organocatalysts such as Jorgensen-Hayashi catalyst and cinchona alkaloid-derivatived catalyst were applied, and novel chiral amine catalysts were developed for these reactions. Stereospecific derivatizations of the chiral halogenated compounds via nucleophilic substitution are also discussed, resulting in the synthesis of many novel chiral compounds that have not been reported before, even as racemates.