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Title

Chiral half-sandwich ruthenium(II) complexes as catalysts in 1,3-dipolar cycloaddition reactions of nitrones with methacrolein

AuthorsCarmona, Daniel ; Lamata, M. Pilar ; Viguri, Fernando ; Ferrer, Joaquina ; García, Néstor; Lahoz, Fernando J. ; Martín, M. Luisa; Oro, Luis A.
KeywordsAsymmetric catalysis
Cycloadditions
Ruthenium
Phosphanyloxazolines
Half-sandwich complexes
Issue Date19-Jul-2006
PublisherWiley-VCH
CitationEuropean Journal of Inorganic Chemistry 2006(16): 3155 - 3166 (2006)
AbstractRuthenium complexes of formula [(6-arene)Ru(LL*)(H2O)][SbF6]2 (arene = C6H6, p-MeC6H4iPr, C6Me6; LL* = bidentate chelate chiral ligand with PN, PP or NN donor atoms) have been tested as catalyst precursors for the asymmetric 1,3-dipolar cycloaddition of nitrones to methacrolein. The reaction occurs quantitatively with perfect endo selectivity and moderate enantioselectivity (up to 74 % ee). The ruthenium aqua complexes can be prepared from the corresponding chlorides, [(6-arene)RuCl(LL*)][SbF6]. Dipolarophile intermediates [(6-arene)Ru(PNiPr)(methacrolein)][SbF6]2 {PNiPr = (4S)-2-(2-diphenylphosphanylphenyl)-4-isopropyl-1,3-oxazoline} as well as nitrone-containing complexes [(p-MeC6H4iPr)Ru(PNiPr)(nitrone)][SbF6]2 (nitrone = N-benzylidenephenylamine N-oxide, N-benzylidenemethylamine N-oxide, 3,4-dihydroisoquinoline N-oxide) have been also isolated and characterised. The crystal structures of the chlorides (RRu)-[(6-C6Me6)RuCl(PNiPr)][SbF6], (RRu)-[(6-C6H6)RuCl(PNInd)][SbF6] {PNInd = (3aR,8aS)-2-[2-(diphenylphosphanyl)phenyl]-3a,8a-dihydroindane[1,2-d]oxazole} and those of the aqua solvates (RRu)-[(6-arene)Ru(PNiPr)(H2O)][SbF6]2 (arene = C6H6, C6Me6) were determined by X-ray diffraction methods.
Description12 pages, 5 tables, scheme 5.
Publisher version (URL)http://dx.doi.org/10.1002/ejic.200600408
URIhttp://hdl.handle.net/10261/19398
DOI10.1002/ejic.200600408
ISSN1521-4095
Appears in Collections:(ICMA) Artículos
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