Catalytic hydrogenation of all-trans-retinal to all-trans-retinol with ruthenium complexes

Allmang, G.; Grass, F.; Grosselin, Jean Michel.; Mercier, C.

doi:10.1016/0304-5102(91)80005-n

Cited by 17 publications

(2 citation statements)

References 10 publications

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“…Heterogeneous enantioselective hydrogenation of diketones on cinchona alkaloid modified platinum represents a promising route for the synthesis of chiral molecules with high optical purity [1][2][3]. As catalysts Pt, Pd and Ir supported on SiO 2 , Al 2 O 3 among others are used [4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

ENANTIOSELECTIVE HYDROGENATION OF 1-PHENYL-1,2-PROPANODIONE ON Pt/ ZrO2 CATALYSTS

Urbina¹,

Pecchi²,

Campos³

et al. 2010

J. Chil. Chem. Soc.

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The enantioselective hydrogenation of 1-phenyl-1,2-propanedione at 298K and pressure of 40 bar of H 2 over zirconia supported Pt catalysts has been studied. Three different zirconia were prepared : i) ZrO 2-P obtained by a precipitation procedure from ZrOCl 2 ii) MSZrO 2 obtained by a sol-gel procedure using cetryltrimethylammonium bromide (CTMABR) as surfactant to get a mesostructured solid iii) CNTsZrO 2 obtained after impregnation of carbon nanotubes with ZrO(NO) 3 followed by pyrolisis and calcination. Pt (1wt%) was introduced on the support by impregnation of an aqueous solution of H 2 PtCl 6. The catalysts were characterized by nitrogen adsorption-desorption isotherms at 77 K, hydrogen chemisorption, XRD and TEM techniques. The reactions were carried out in a stainless steel batch reactor using cyclohexane as solvent and cinchonidine as chiral modifier. The presence of CD in the reaction medium is necessary to induce an enantiomeric excess (ee) of the desired product R-1phenyl-1 hydroxi-2-propanone. In all the studied systems, the relation between the enantioselectivity and the CD concentration added in situ exhibits a bell type curve; indicative of the importance of competitive adsorption between the modifier and the substrate on the catalyst surface. On the other hand, confinement effect led to an important enhancement in the activity in those catalysts supported on mesostructured supports, mainly in the Pt/CNTsZrO 2 catalyst.

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Section: Introductionmentioning

confidence: 99%

ENANTIOSELECTIVE HYDROGENATION OF 1-PHENYL-1,2-PROPANODIONE ON Pt/ ZrO2 CATALYSTS

Urbina¹,

Pecchi²,

Campos³

et al. 2010

J. Chil. Chem. Soc.

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“…[1][2][3][4] Thus, the synthesis of chiral compounds is of growing interest; among them, the hydrogenation of a-ketoesters and ketones is the most widely studied. [5][6][7][8][9][10][11][12][13][14][15] Since Orito et al reported the enantioselective hydrogenation of ethyl pyruvate to (R)-ethyl lactate over cinchonidine-modified Pt catalysts with ee's up to 95%, many other research teams have evaluated the performance of their catalytic systems in this reaction.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective hydrogenation of ethyl pyruvate and 1-phenyl-1,2-propanedione on catalysts prepared by impregnation of colloidal platinum on SiO2

Ruiz¹,

Fierro²,

Reyes³

2010

J. Braz. Chem. Soc.

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A hidrogenação enantiosseletiva de piruvato de etila e de 1-fenil-1,2-propanodiona foi estudada a 298 K e sob 40 bar de H 2 sobre um catalisador de platina coloidal estabilizado com cinchonidina (CD) e suportado em sílica. O catalisador foi preparado por impregnação da platina coloidal em sílica, atingindo 1% em massa do metal no suporte. O colóide foi preparado a partir de uma solução aquosa de H 2 PtCl 6 estabilizada com diferentes quantidades de CD. O catalisador foi caracterizado por isotermas de adsorção-desorção de N 2 a 77 K e por XPS, XRD e TEM. As reações foram efetuadas em batelada em um reator de aço inoxidável, usando cicloexano como solvente e cinchonidina como modificador quiral. A adição de CD ao catalisador permite a estabilização e o controle do tamanho de partícula da platina, e também afeta o excesso enantiomérico (ee) do sistema, levando a um maior rendimento do produto com configuração R. A relação entre a concentração de CD adicionada in situ e a enantiosseletividade apresenta uma curva do tipo sino nas duas reações estudadas; este comportamento é um indicativo da importância da adsorção competitiva do modificador e do substrato na superfície do catalisador.The enantioselective hydrogenation of ethyl pyruvate and 1-phenyl-1,2-propanedione was studied at 298 K and 40 bar of H 2 over colloidal Pt stabilized with cinchonidine (CD) and supported on silica. The catalysts were prepared by impregnation of colloidal Pt on SiO 2 , leading to a metal load close to 1 wt.%. The colloid was prepared from an aqueous solution of H 2 PtCl 6 and stabilized with different quantities of CD. The catalysts were characterized by nitrogen adsorption-desorption isotherms at 77 K, XPS, XRD and TEM techniques. The reactions were carried out in a stainless steel batch reactor using cyclohexane as solvent and cinchonidine as chiral modifier. The addition of CD to the catalysts allows the stabilization and control of the platinum particle size and also affects the enantiomeric excess (ee) of the system, affording a higher proportion of the (R)-product. The relationship between the enantioselectivity and the CD concentration (added in situ) exhibits a bell type curve for both reactions, this being indicative of the importance of a competitive adsorption of the modifier and substrate on the catalyst surface.Keywords: Pt colloids, enantioselectivity, ethyl pyruvate, 1-phenyl-1,2-propanedione, cinchonidine IntroductionEnantioselective hydrogenation reactions are important tools to obtain fine chemicals used in pharmaceutical and food products.1-4 Thus, the synthesis of chiral compounds is of growing interest; among them, the hydrogenation of a-ketoesters and ketones is the most widely studied. [5][6][7][8][9][10][11][12][13][14][15] Since Orito et al. reported the enantioselective hydrogenation of ethyl pyruvate to (R)-ethyl lactate over cinchonidine-modified Pt catalysts with ee's up to 95%, many other research teams have evaluated the performance of their catalytic systems in this reaction. [16][17][18] Indeed, this is n...

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Organometallic Compounds and Homogeneous Catalysis

Behr

2000

Ullmann's Encyclopedia of Industrial Chemistry

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Catalytic hydrogenation of all-trans-retinal to all-trans-retinol with ruthenium complexes

Cited by 17 publications

References 10 publications

ENANTIOSELECTIVE HYDROGENATION OF 1-PHENYL-1,2-PROPANODIONE ON Pt/ ZrO2 CATALYSTS

ENANTIOSELECTIVE HYDROGENATION OF 1-PHENYL-1,2-PROPANODIONE ON Pt/ ZrO2 CATALYSTS

Enantioselective hydrogenation of ethyl pyruvate and 1-phenyl-1,2-propanedione on catalysts prepared by impregnation of colloidal platinum on SiO2

Organometallic Compounds and Homogeneous Catalysis

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