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Chiral transition-metal complexes as Brønsted-acid catalysts for the asymmetric Friedel-Crafts hydroxyalkylation of indoles

AuthorsCarmona, Daniel ; Lamata, M. Pilar ; Sánchez, Antonio; Viguri, Fernando ; Rodríguez, Ricardo ; Oro, Luis A. ; Liu, Chunhui; Díez-González, Silvia; Maseras, Feliu
Issue Date2014
PublisherRoyal Society of Chemistry (UK)
CitationDalton Transactions 43(29): 11260-11268 (2014)
AbstractThe Friedel-Crafts reaction between 3,3,3-trifluoropyruvates and indoles is efficiently catalysed by the iridium complex [(η5-C 5Me5)Ir{(R)-Prophos}(H2O)][SbF 6]2 (1) with up to 84% ee. Experimental data and theoretical calculations support a mechanism involving the Brønsted-acid activation of the pyruvate carbonyl by the protons of the coordinated water molecule in 1. Water is not dissociated during the process and, therefore, the catalytic reaction occurs with no direct interaction between the substrates and the metal. This journal is © the Partner Organisations 2014.
Identifiersdoi: 10.1039/C4DT00556B
issn: 1477-9226
e-issn: 1477-9234
Appears in Collections:(ISQCH) Artículos
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