Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates
Albert Granados1, Anna Ballesteros1, Adelina Vallribera1
1Department of Chemistry and Centro de Innovación en Quı́mica Avanzada (ORFEO-CINQA), Universitat Autònoma de Barcelona, Cerdanyola del Vallès, 08193 Barcelona, Spain.
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.
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