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Chiral octahedral phosphano-oxazoline iridium(III) complexes as catalysts in asymmetric cycloaddition reactions

AuthorsCarmona, Daniel CSIC ORCID; Ferrer, Joaquina CSIC ORCID; García, Néstor CSIC; Ramírez, Paola; Lahoz, Fernando J. CSIC ORCID; García-Orduña, P. CSIC ORCID; Oro, Luis A. CSIC ORCID
Issue Date2013
PublisherAmerican Chemical Society
CitationOrganometallics 32(6): 1609-1619 (2013)
AbstractThe 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.
Identifiersdoi: 10.1021/om301089c
issn: 0276-7333
e-issn: 1520-6041
Appears in Collections:(ISQCH) Artículos
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