Resolutions using metal complexes. Synthesis, separation into diastereoisomers, and resolution of o-phenylenebis(methylphenylphosphine) using palladium complexes containing optically active ortho-metalated dimethyl(.alpha.-methylbenzyl)amines

Roberts, Nicholas K.; Wild, S. Bruce

doi:10.1021/ja00515a016

Cited by 135 publications

(47 citation statements)

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“…23 Cyclometalations that are assisted by oxygen, arsenic, and selenium donors are also known, though they are much rarer. 149,150 Chirality has been incorporated, for example through asymmetric ligand synthesis, [426][427][428][429][430] 436 Monomers are also present in solvents like benzene at high temperatures.…”

Section: Scheme 108mentioning

confidence: 99%

Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends

2009

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Section: Scheme 108mentioning

confidence: 99%

Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends

2009

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“…[32] The (S,S) and (R,S) diastereomers of both 8 and 9 showed two separate sets of doublets in the 31 P NMR spectrum. These palladium complexes were prepared by stirring BIFAP or BIFAPS with one equivalent of di(m-chloro)bis[(S)-dimethyl(a-methylbenzyl)aminato-C 2 N]dipalladium(ii) in methanol for about 15 min at room temperature.…”

Section: Resultsmentioning

confidence: 93%

Synthesis of the Dibenzofuran-Based Diphosphine Ligand BIFAP and Its Water-Soluble Derivative BIFAPS and Their Use in Ruthenium-Catalyzed Asymmetric Hydrogenation.

Gelpke¹,

Kooijman²,

Spek³

et al. 1999

Chem. Eur. J.

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The syntheses of both enantiomers of the novel diphosphine ligand 2,2'-bis(diphenylphosphanyl)-1,1'-bidibenzofuranyl (BIFAP, 1) and the water-Advantage is taken of the very high regioselectivity in ring functionalisation of the 1,1'-bidibenzofuranyl backbone. These ligands are used in the ruthenium-catalysed hydrogenation of methyl acetoacetate and (Z)-acetamidocinnamic acid in methanol and water. In methanol both BIFAP and BIFAPS give the products in very high enantiomeric excess. With BIFAPS in water a slight drop in the ee of the products is observed. When BIFAPS is used with either water or methanol as the solvent the addition of a small amount of acid turns out to be essential for a fast reaction and high asymmetric induction.

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“…Methylphenylphosphine was distilled and kept under argon [13]. n-Butyllithium and iodomethane were used as supplied by Sigma-Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Reactivity of phosphiranes toward nucleophiles: Theoretical and experimental investigations

Coote

Krenske

Maulana

et al. 2008

Heteroatom Chemistry

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Resolutions using metal complexes. Synthesis, separation into diastereoisomers, and resolution of o-phenylenebis(methylphenylphosphine) using palladium complexes containing optically active ortho-metalated dimethyl(.alpha.-methylbenzyl)amines

Cited by 135 publications

References 1 publication

Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends

Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends

Synthesis of the Dibenzofuran-Based Diphosphine Ligand BIFAP and Its Water-Soluble Derivative BIFAPS and Their Use in Ruthenium-Catalyzed Asymmetric Hydrogenation.

Reactivity of phosphiranes toward nucleophiles: Theoretical and experimental investigations

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