Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates

Abstract

An electrophilic enantioselective catalytic method for the α-pentafluoroethylation of 3-oxoesters is described. Under the use of La(OTf)3 in combination with a (S,R)-indanyl-pybox ligand, good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions, leading to the formation of enantioenriched quaternary centers. This methodology uses an hypervalent iodine(III)-CF2CF3 reagent, and mechanistic investigations are consistent with the involvement of a radical pathway.