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Half-Sandwich Rhodium (and Iridium) Complexes as Enantioselective Catalysts for the 1,3-Dipolar Cycloaddition of 3,4-Dihydroisoquinoline N-Oxide to Methacrylonitrile.

AuthorsCarmona, Daniel ; Lamata, M. Pilar ; Viguri, Fernando ; Rodríguez, Ricardo ; Lahoz, Fernando J. ; Oro, Luis A.
KeywordsAsymmetric catalysis
Issue Date30-Oct-2007
CitationChemistry - A European Journal 13(35): 9746-9756 (2007)
AbstractCationic half-sandwich complexes containing the [(5-C5Me5)M(Diphos*)] moiety (M=Rh, Ir; Diphos*=chiral diphosphine ligand) catalyze the cycloaddition of the nitrone 3,4-dihydroisoquinoline N-oxide (A) to methacrylonitrile (B) with excellent regio and endo selectivity and low-to-moderate enantioselectivity. The most active and selective catalyst, (SRh,RC)-[(5-C5Me5)Rh{(R)-Prophos)} (NC(Me)CCH2)](SbF6)2, has been isolated and fully characterized including the determination of the molecular structure by X-ray diffraction. The R-at-metal epimers of the complexes [(5-C5Me5)M{(R)-Prophos)}(NC(Me)CCH2)](SbF6)2 (M=Rh, Ir) isomerize to the corresponding S-at-metal diastereomers. The stoichiometric cycloaddition of A with B is catalyzed by diastereopure (SM,RC)-[(5-C5Me5)M{(R)-Prophos)}(NC(Me)CCH2)](SbF6)2 with perfect regio and endo selectivity and very good (up to 95 %) ee. The catalyst can be recycled up to nine times without significant loss of either activity or selectivity.
Description11 pages, 2 figures, 6 tables.
Publisher version (URL)http://dx.doi.org/10.1002/chem.200701140
Appears in Collections:(ICMA) Artículos
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