Synthesis and Characterisation of New Iridium Complexes with the (4S)-2-[2-(Diphenylphosphanyl)phenyl]-4-isopropyl-1,3-oxazoline Ligand That Catalyse Asymmetric Michael Reactions

The chiral iridium compounds [IrCl(COE){(S)‐PN}] {COE = cyclooctene, PN = (4S)‐2‐[2‐(diphenylphosphanyl)phenyl]‐4‐isopropyl‐1,3‐oxazoline, (1)}, [Ir(acac)ClH{(S)‐PN}] {Hacac = acetylacetone, (2)} and [Ir{(S)‐PN}2]A {A = Cl (3a,b); BF4 (4a,b); PF6 (5a,b)} have been prepared, characterised and employe...

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Bibliographic Details
Published in:European Journal of Inorganic Chemistry 2005, Vol.2005 (9), p.1657-1664
Main Authors: Carmona, Daniel, Ferrer, Joaquina, Lorenzo, Mónica, Lahoz, Fernando J., Dobrinovitch, Isabel T., Oro, Luis A.
Format: Review
Language:English
Subjects:
Iridium
Metal enolates
Michael addition
Phosphanyloxazolines
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Summary:The chiral iridium compounds [IrCl(COE){(S)‐PN}] {COE = cyclooctene, PN = (4S)‐2‐[2‐(diphenylphosphanyl)phenyl]‐4‐isopropyl‐1,3‐oxazoline, (1)}, [Ir(acac)ClH{(S)‐PN}] {Hacac = acetylacetone, (2)} and [Ir{(S)‐PN}2]A {A = Cl (3a,b); BF4 (4a,b); PF6 (5a,b)} have been prepared, characterised and employed as catalysts for the asymmetric Michael addition of keto or cyano esters to α,β‐unsaturated carbonyl compounds. The X‐ray molecular structures of compounds 2 and 5b are reported. The model catalytic intermediates [IrH(NCCHCO2R){(S)‐PN}2]Cl {R = Me (12), Et (13)} have also been isolated and characterised. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.200400929