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

Year: 2020

Type: article

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)-CF 2 CF 3 reagent, and mechanistic investigations are consistent with the involvement of a radical pathway.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.0c00210

Authors: Albert Granados, Anna Ballesteros, Adelina Vallribera

Institutions: Universitat Autònoma de Barcelona, ORFEO-CINQA Research Network

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green