New efficient methods for the synthesis and in-situ preparation of ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations

Heiser, B.; Broger, Emil A.; Crameri, Yvo

doi:10.1016/s0957-4166(00)82157-6

Cited by 158 publications

(49 citation statements)

References 8 publications

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“…The number of publications on ruthenium catalyzed hydrogenations of dimethyl itaconate is rather small [6] and an excellent chiral catalyst to date is [Ru(BINAP)(CH 3 CN) (cod)]BF 4 which leads to the formation of dimethyl succinate (8) with an enantiomeric excess of 95%. [7] …”

Section: Resultsmentioning

confidence: 99%

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New Route to Biaryl Phosphanes with Axial Chirality as Ligands for Enantioselective Hydrogenations

Drießen‐Hölscher¹,

Kralik²,

Agel³

et al. 2004

Adv Synth Catal

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Section: Resultsmentioning

confidence: 99%

“…[8] Formation of the complexes {[(R)-1a ± e]Ru(OOCCF 3 ) 2 } is complete after 70 hours at room temperature. The isolated compounds are yellow or orange solids which have been characterized by 31 P NMR spectroscopy.…”

Section: Full Papersmentioning

confidence: 99%

New Route to Biaryl Phosphanes with Axial Chirality as Ligands for Enantioselective Hydrogenations

Drießen‐Hölscher¹,

Kralik²,

Agel³

et al. 2004

Adv Synth Catal

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“…However, in contrast to 1 which reacts cleanly with CF 3 CO 2 H to give [Ru(η 4 -C 8 H 12 )(µ-O 2 CCF 3 ) 2 ] 2 , [8] treatment of 2 or 3 with trifluoroacetic acid leads to a mixture of products which could not be separated by conventional techniques.…”

Section: Resultsmentioning

confidence: 99%

Six-Coordinate Ruthenium(II) Complexes Containing Unsymmetrical 1,2-Bis(phosphanyl)ethanes and 1-Arsanyl-2-phosphanylethanes as Ligands

Fries

Ilg

Pfeiffer

et al. 2000

Eur. J. Inorg. Chem.

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The bis(η3‐2‐methallyl)ruthenium(II) complexes [Ru(η3‐2‐MeC3H4)2(κ2‐Ph2PCH2CH2PR2)] [R = iPr (2), Cy (3)] were prepared from the cycloocta‐1,5‐diene derivative [Ru(η3‐2‐MeC3H4)2(η4‐C8H12)] (1) and the unsymmetrical 1,2‐bis(phosphanyl)ethanes Ph2PCH2CH2PR2. The As,P analogue [Ru(η3‐2‐MeC3H4)2(κ2‐Ph2PCH2CH2AstBu2)] (4) was obtained by the same route. The reaction of 2 with hexafluoroacetylacetone afforded the chelate compound [Ru(κ2‐[F6]acac)2(κ2‐iPr2PCH2CH2PPh2)], whereas treatment of 2 and 3 with pentachlorophenol gave the related, more labile complexes [Ru(κ2‐O,Cl‐OC6Cl5)2(κ2‐R2PCH2CH2PPh2)] [R = iPr (6), Cy (7)]. Preparation of the parent bis(acac) compound [Ru(κ2‐acac)2(κ2‐iPr2PCH2CH2PPh2)] (8), which could not be obtained from 2 and acacH, was achieved by ligand exchange of 6 and acetylacetone. The molecular structures of 2 and 6 were determined by X‐ray crystallography.

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“…This process is derived from procedures that were developed by one of us [13] and in parallel by Heiser et al [14] These groups treated 6 with approximately two equivalents of acids that contain coordinating conjugate bases (HCl, HBr, HI, and CF 3 CO 2 H, respectively). Both [*] Dr.…”

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confidence: 99%

Industrial Synthesis of (+)-cis-Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst [Ru((−)-Me-DuPHOS)(H)(η6-1,3,5-cyclooctatriene)](BF4)

Dobbs

Vanhessche

Brazi

et al. 2000

Angew. Chem. Int. Ed.

141

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Prototypes of new families of precatalysts and catalysts, [Ru((−)‐Me‐DuPHOS)(H)(η6‐1,3,5‐cyclooctatriene)](BF4) and the derived “[Ru((−)‐Me‐DuPHOS)(H)(sol)](BF4)”, are presented. They are used in an industrial, catalytic, enantioselective hydrogenation that leads to (+)‐cis‐methyl dihydrojasmonate [Eq. (1)]. This stereoisomer is the odorant component of an important, large volume perfumery chemical. P−P=Diphosphane ligand (for example, Me‐DuPHOS=1,2‐bis((2R,5R)‐2,5‐dimethylphospholanyl)benzene); sol=solvent.

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New efficient methods for the synthesis and in-situ preparation of ruthenium(II) complexes of atropisomeric diphosphines and their application in asymmetric catalytic hydrogenations

Cited by 158 publications

References 8 publications

New Route to Biaryl Phosphanes with Axial Chirality as Ligands for Enantioselective Hydrogenations

New Route to Biaryl Phosphanes with Axial Chirality as Ligands for Enantioselective Hydrogenations

Six-Coordinate Ruthenium(II) Complexes Containing Unsymmetrical 1,2-Bis(phosphanyl)ethanes and 1-Arsanyl-2-phosphanylethanes as Ligands

Industrial Synthesis of (+)-cis-Methyl Dihydrojasmonate by Enantioselective Catalytic Hydrogenation; Identification of the Precatalyst [Ru((−)-Me-DuPHOS)(H)(η6-1,3,5-cyclooctatriene)](BF4)

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