(−)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane a new chiral ligand for enantioselective catalysis

Chelucci, Giorgio; Cabras, M. A.; Botteghi, C.; Marchetti, Mauro

doi:10.1016/s0957-4166(00)86190-x

Cited by 40 publications

(13 citation statements)

References 12 publications

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“…The chiral compound L was obtained from dimethyl (+)-Ltartrate in enantiomerically pure form through the complex reaction sequence described previously. 6 The compound [PdLCl,] 1 was synthesized in fairly good yield (ca. 80%) from trans-[Pd(PhCN),Cl,].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of square-planar palladium(II), platinum(II) and rhodium(I) complexes with a chiral pyridylphosphine hybrid ligand

Stoccoro¹,

Chelucci²,

Zucca³

et al. 1996

J. Chem. Soc., Dalton Trans.

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The complexes [PdLCl,] 1, [PtLCl,] 2, [PtL(SnCI,)Cl] 3 and [RhL(CO)CI] 4, where L is the chiral pyridylphosphine 4-(diphenylphosphinomet hyl)-2,2-dimethyl-5-(2-pyridyl)-1 ,3-dioxolane7 have been synthesized and characterized by IR, NMR and FAB mass spectra. The structure of compound 1 has been solved by X-ray diffraction: the ligand is co-ordinated through both the P and N atoms to form a seven-membered ring which adopts a chair conformation. One of the hydrogen atoms of the backbone is located 2.72(3) A over the palladium atom in a pseudo-axial position. Spectroscopic evidence supports a chelating behaviour of the ligand also in compounds 2 and 3. The behaviour of the L ligand in the rhodium(1) species 4 is discussed.

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Section: Resultsmentioning

confidence: 99%

“…4,5-bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane], has recently been synthesized by some of us. 6 We deemed it worthwhile to evaluate its behaviour with d8 metal ions, namely Pd", Pt" and Rh', and here report the first results. A preliminary account of this work has been given.…”

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confidence: 99%

Synthesis and characterization of square-planar palladium(II), platinum(II) and rhodium(I) complexes with a chiral pyridylphosphine hybrid ligand

Stoccoro¹,

Chelucci²,

Zucca³

et al. 1996

J. Chem. Soc., Dalton Trans.

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“…In the case of rhodium catalysts, Marchetti et al studied the use of pyridylphosphine Pydiphos 264 and its P-oxide 265 as ligands (Scheme ). The hydroformylation reactions were carried out at 90 bar of CO/H 2 (1:1) with a substrate to [Rh(CO) 2 (acac)] ratio of 300:1.…”

Section: Viii62 Enantioselective Hydroformylationmentioning

confidence: 99%

Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

et al. 2000

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“…The formation of complexes by phosphine 100 (PYDIPHOS) was thoroughly studied by spectral methods (IR spectroscopy, 31 P, 1 H and 13 C NMR spectroscopy) and mass spectrometry. 133,134 Both rhodium (101) and palladium (102) metal complexes were described as chelates (the structure of the complex 102 was confirmed by X-ray diffraction analysis); however, the data obtained for the complex 101 do not rule out unambiguously an alternative highly symmetrical binuclear structure with bridging coordination of the P,N-bidentate ligands of the `head-to-tail' type. 134 The enantioselectivity observed in catalytic reactions involving PYDIPHOS (100) is moderate.…”

Section: Ligands With Sp 2 -Hybridised Electron-donating Nitrogen Atomsmentioning

confidence: 99%

Chiral P,N-bidentate ligands in coordination chemistry and organic catalysis involving rhodium and palladium

Gavrilov¹,

Polosukhin²

2000

Russ. Chem. Rev.

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Published data on the synthesis of rhodium and palla-Published data on the synthesis of rhodium and palladium complexes with optically active P,N-bidentate ligands and dium complexes with optically active P,N-bidentate ligands and their applications in homogeneous asymmetric catalysis are their applications in homogeneous asymmetric catalysis are summarised and discussed. The effect of the nature of the P,N-summarised and discussed. The effect of the nature of the P,Nbidentate compounds on the structure of the metal complexes and bidentate compounds on the structure of the metal complexes and on enantioselectivity in catalysis is examined. Allylic substitution, on enantioselectivity in catalysis is examined. Allylic substitution, cross-coupling, hydroboration and hydrosilylation catalysed by cross-coupling, hydroboration and hydrosilylation catalysed by Rh or Pd complexes with optically active P,N-bidentate ligands Rh or Pd complexes with optically active P,N-bidentate ligands are considered. The prospects for the development of this field of are considered. The prospects for the development of this field of chemistry are demonstrated. The bibliography includes 186 refer-chemistry are demonstrated. The bibliography includes 186 references ences. .

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(−)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane a new chiral ligand for enantioselective catalysis

Cited by 40 publications

References 12 publications

Synthesis and characterization of square-planar palladium(II), platinum(II) and rhodium(I) complexes with a chiral pyridylphosphine hybrid ligand

Synthesis and characterization of square-planar palladium(II), platinum(II) and rhodium(I) complexes with a chiral pyridylphosphine hybrid ligand

Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Chiral P,N-bidentate ligands in coordination chemistry and organic catalysis involving rhodium and palladium

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