Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates
Granados Toda, Albert (Universitat Autònoma de Barcelona. Departament de Química)
Ballesteros, Anna (Universitat Autònoma de Barcelona. Departament de Química)
Vallribera Massó, Adelina (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2020
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.
Grants:	Agencia Estatal de Investigación RTI2018-097853-B-I00 Agencia Estatal de Investigación CTQ2016-81797-REDC Agencia Estatal de Investigación RED2018-102387-T Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR-465
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Alkyls ; Ligands ; Mixtures ; Organic compounds ; Reagents
Published in:	Journal of organic chemistry, Vol. 85, Issue 16 (August 2020) , p. 10378-10387, ISSN 1520-6904

DOI: 10.1021/acs.joc.0c00210

Postprint 24 p, 966.5 KB

The record appears in these collections:
Articles > Research articles
Articles > Published articles