Stereoisomeric 2-butylphenylsulfoxides and their binding modes in the adduct formation with an enantiopure dirhodium tetracarboxylate complex

Mattiza, Jens T.; Meyer, Vera J.; Duddeck, H.

doi:10.1016/j.molstruc.2010.01.060

Cited by 6 publications

(2 citation statements)

References 34 publications

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“…These salts act as chiral recognition agents. By this, one could determine either the optical purity of a compound or, in certain cases, its absolute configuration . For the proper application of dirhodium methods, it is essential to know the plausible adduct structures and the details of complexation processes.…”

Section: Introductionmentioning

confidence: 99%

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations

Jaźwiński

Sadlej

2013

Magnetic Reson in Chemistry

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The complexation of rhodium(II) tetraacetate, tetrakistrifluoroaceate and tetrakisoctanoate with a set of diamines (ethane-1,diamine, propane-1,3-diamine and nonane-1,9-diamine) and their N,N'-dimethyl and N,N,N',N'-tetramethyl derivatives in chloroform solution has been investigated by (1) H and (13) C NMR spectroscopy and density functional theory (DFT) modelling. A combination of two bifunctional reagents, diamines and rhodium(II) tetracarboxylates, yielded insoluble coordination polymers as main products of complexation and various adducts in the solution, being in equilibrium with insoluble material. All diamines initially formed the 2 : 1 (blue), (1 : 1)n oligomeric (red) and 1 : 2 (red) axial adducts in solution, depending on the reagents' molar ratio. Adducts of primary and secondary diamines decomposed in the presence of ligand excess, the former via unstable equatorial complexes. The complexation of secondary diamines slowed down the inversion at nitrogen atoms in NH(CH3 ) functional groups and resulted in the formation of nitrogenous stereogenic centres, detectable by NMR. Axial adducts of tertiary diamines appeared to be relatively stable. The presence of long aliphatic chains in molecules (adducts of nonane-1,9-diamines or rhodium(II) tetrakisoctanoate) increased adduct solubility. Hypothetical structures of the equatorial adduct of rhodium(II) tetraacetate with ethane-1,2-diamine and their NMR parameters were explored by means of DFT calculations.

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Section: Introductionmentioning

confidence: 99%

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations

Jaźwiński

Sadlej

2013

Magnetic Reson in Chemistry

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“…Enantiomeric differentiation of sulfoxides is easily accomplished by the dirhodium experiment, i.e., recording the NMR spectra in the presence of an equimolar amount of 67. Complex formation shifts ( ) and diastereomeric dispersion effects ( ) differed in the dirhodium experiment for nonracemic mixtures of sulfoxides when compared with the pure enantiomers and this did not affect the efficiency of the dirhodium experiment [102].…”

Section: Elucidation By Formation Of Adductsmentioning

confidence: 98%

Chiral Dirhodium Catalysts: A New Era for Asymmetric Catalysis

El‐Deftar¹,

Adly²,

Gardiner

et al. 2012

COC

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The catalysis by dirhodium paddlewheel complexes has been an area of immense interest and extensive study over the past three decades -not only because most of the catalysts are highly stable to heat, moisture and ambient atmosphere but also for the asymmetric induction in the ylide generation. In this review, we attempt to provide an overview on the general preparation method for most homogeneous chiral dirhodium(II) catalysts that have appeared to date and their recent applications in asymmetric catalysis with iodonium ylides as carbenoid precursors.

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Duddeck, Helmut: Molecular Structures in Three Dimensions

Duddeck

2010

Encyclopedia of Magnetic Resonance

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Stereoisomeric 2-butylphenylsulfoxides and their binding modes in the adduct formation with an enantiopure dirhodium tetracarboxylate complex

Cited by 6 publications

References 34 publications

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations

Chiral Dirhodium Catalysts: A New Era for Asymmetric Catalysis

Duddeck, Helmut: Molecular Structures in Three Dimensions

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Stereoisomeric 2-butylphenylsulfoxides and their binding modes in the adduct formation with an enantiopure dirhodium tetracarboxylate complex

Cited by 6 publications

References 34 publications

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: 1H and 13C NMR and DFT investigations

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: 1H and 13C NMR and DFT investigations

Chiral Dirhodium Catalysts: A New Era for Asymmetric Catalysis

Duddeck, Helmut: Molecular Structures in Three Dimensions

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Product

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Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations

Complexation of rhodium(II) tetracarboxylates with aliphatic diamines in solution: ¹H and ¹³C NMR and DFT investigations