Organocatalytic asymmetric fluorination/semipinacol rearrangement: An efficient approach to chiral β-fluoroketones

摘要

Chiral fluorinated molecules have attractive properties for agricultural, medicinal, and material applications. Therefore, the introduction of carbon fluorine bonds in an asymmetric manner is of great importance in modern synthetic chemistry, and the development of methodologies that achieve this transformation are in high demand. The fluorination/semipinacol rearrangement, which is initiated by fluorination of the double bond, is a straightforward strategy for the preparation of b-fluorocarbonyl compounds, which are potentially useful compounds for fluorine chemistry. All substrates afforded the desired chiral b-fluoroketone derivatives in moderate to good yields with moderate to excellent levels of enantioselectivity. Various enantioselective transformations promoted by these catalysts have been achieved. Recently, the research group and that of others have reported some examples of asymmetric bromination/semipinacol rearrangement reactions that are catalyzed by cinchona-alkaloid derivatives.