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Chiral octahedral phosphano-oxazoline iridium(III) complexes as catalysts in asymmetric cycloaddition reactions
Authors
Daniel Carmona
Joaquina Ferrer
+5 more
Néstor García
P. García-Orduña
Fernando J. Lahoz
Luis A. Oro
Paola Ramírez
Publication date
24 February 2015
Publisher
'American Chemical Society (ACS)'
Doi
Cite
Abstract
The synthesis and characterization of cationic iridium(III) aqua complexes of the formula [IrH(H2O)(PN*)(PP)][SbF6]2 (PN* = chiral phosphano-oxazoline ligand; PP = diphosphane) as well as that of the OPOF2-containing complex [IrH(OPOF2)(PNiPr) (dppp)][SbF6] (10) are reported. The X-ray molecular structures of [IrH(H2O)(PNInd)(dppe)][SbF6]2 (1), [IrH(H 2O)(PNInd)(dppen)][SbF6]2 (2), and 10a have been determined. Dichloromethane solutions of these aqua complexes efficiently catalyze the enantioselective 1,3-dipolar cycloaddition of the nitrone N-benzylidenephenylamine N-oxide to methacrolein and Diels-Alder reactions between cyclopentadiene and trans-β-nitrostyrenes. In the first case, the catalytic reaction occurs with excellent endo selectivity and ee up to 85%; the Diels-Alder reaction occurs rapidly at room temperature with good endo:exo selectivity and ee up to 90%. The dipolar cycloaddition intermediates [IrH(methacrolein)(PNInd)(PP)][SbF6]2 (PP = (S,S)-chiraphos (11), (R)-prophos (12)) have been characterized, and the molecular structure of 11 has been determined by an X-ray structural analysis. © 2013 American Chemical Society.We thank the Ministerio de Educación y Ciencia (Grant CTQ 2009-10303/BQU) and Gobierno de Aragón (Grupo Consolidado: Catalizadores Organometálicos Enantioselectivos) for financial support. This work was supported by the CONSOLIDER INGENIO-2010 program under the project “Factoría de Crystalización” (CSD2006-0015).Peer Reviewe
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Last time updated on 25/05/2016