Increase in activity and enantioselectivity in asymmetric hydrogenation reactions catalysed by chiral rhodium(I) complexes as a consequence of the action of amphiphiles

Oehme, G.; Paetzold, Eckhard; Selke, Rüdiger

doi:10.1016/0304-5102(92)80001-w

Cited by 85 publications

(36 citation statements)

References 15 publications

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“…2 Aqueous micellar media for the asymmetric catalytic hydrogenation of amino acid precursors (Scheme 1) were investigated recently. 3 The activities and enantioselectivities obtained with the rhodium(I) catalyst [Rh(bppm)(cod)]BF 4 in the hydrogenation of (Z)-methyl ␣-acetamidocinnamate in the presence of different types of amphiphiles in water are similar to those obtained in methanol. 4 There are some indications that the reaction takes place within the micelles.…”

supporting

confidence: 51%

Amphiphilic proline and prolylproline derivatives in the rhodium(I)-catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle

et al. 1998

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Proline and prolylproline dipeptide derived surfactants promote the asymmetric hydrogenation of (Z)‐methyl α‐acetamidocinnamate in water in the presence of the catalytic system [Rh(cod)2]BF4 + BPPM. Activity and enantioselectivity are enhanced significantly and the results in water are similar to those obtained with organic solvents. The possibility of a chiral induction was investigated in the presence of the optically active amino acid and peptide amphiphiles and an achiral rhodium catalyst [Rh(bdpb)(cod)]BF4. The analysis of the low optical induction gave some indications of the site where the reaction takes place within the micelle. Selected critical micelle concentrations (cmc) of the new prepared surfactants were determined by surface tension measurements. Chirality 10:754–759, 1998. © 1998 Wiley‐Liss, Inc.

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confidence: 51%

Amphiphilic proline and prolylproline derivatives in the rhodium(I)-catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle

et al. 1998

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“…140 Micelle-forming amphiphiles significantly increase both the reaction rate and the enantioselectivity of Rh(I)-catalyzed hydrogenations of amino acid precursors. 141,142 This enhancement is only observed when the concentration of the surfactant is above its CMC. 143 Water-soluble rhodium complexes containing glucose-based phosphino ligands (63, 64, Chart 2) proved to be effective catalysts in the asymmetric hydrogenation of various enamides and itaconic acid in water in the presence of SDS.…”

Section: Micelle-based Systemsmentioning

confidence: 99%

Self‐Assembled Nanoreactors

et al. 2005

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“…Practically no conversion was observed using Quinap as the ligand in the presence of a neutral surfactant such as Tween 40 (Table 6, entry 9). Finally, the bisoxazoline ligand Ph-Box gave no reaction at all in the presence of CTAHSO 4 or Tween 40 (Table 6, entries 12 and 13). The very low activities observed in the case of ligands bearing an imine function (Josiphos, Ph-Box) could be due to the hydrolysis of this double bond in water; as the reaction did not occur in the presence of a neutral surfactant, the possible quaternization of the nitrogen by the cationic surfactant can be excluded.…”

Section: Full Papersmentioning

confidence: 98%

Catalytic Asymmetric Alkylation in Water in the Presence of Surfactants

2003

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Asymmetric palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate occurs in water in the presence of surfactants and a base. The efficiency as well as the enantioselectivity of the coupling reaction depend strongly on the nature and the concentration of the surfactant. The highest yield and enantioselectivity (up to 91%) was obtained using Binap as the ligand in the presence of a cationic surfactant, while neutral or zwitterionic surfactants gave poorer results; anionic surfactants gave no reaction at all. The best results were obtained using Na 2 CO 3 , NaHCO 3 , or K 2 CO 3 , among the bases used. The highest enantioselectivities were obtained when the reaction was performed in the presence of chiral atropoisomeric diphosphines such as Binap, Biphemp, or MeOBiphep. A supported cationic surfactant was also used successfully in this reaction, allowing an easier separation of the product.

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Increase in activity and enantioselectivity in asymmetric hydrogenation reactions catalysed by chiral rhodium(I) complexes as a consequence of the action of amphiphiles

Cited by 85 publications

References 15 publications

Amphiphilic proline and prolylproline derivatives in the rhodium(I)-catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle

Amphiphilic proline and prolylproline derivatives in the rhodium(I)-catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle

Self‐Assembled Nanoreactors

Catalytic Asymmetric Alkylation in Water in the Presence of Surfactants

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