Enantio- and chemoselective reduction of 2,4-diketo acid derivatives with cinchona modified Pt-catalyst—Synthesis of (R)-2-hydroxy-4-phenylbutyric acid ethyl ester

Studer, Martin; Burkhardt, Stefan; Indolese, Adriano F.; Blaser, Hans‐Ulrich

doi:10.1039/b002538k

Cited by 44 publications

(20 citation statements)

References 10 publications

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“…Here a conventional heterogeneous catalyst, such as platinum or raney nickel, is modified by treatment with readily available chiral substances . Although the overall success of this approach has been limited, platinum on alumina modified by cinchona alkaloids has been found to be a particularly effective catalyst for the enantioselective hydrogenation of α-ketoesters in general and pyruvate esters in particular [21][22][23][24][25][26][27][28][29][30][31][32][33]. This reaction is commonly referred to as the Orito reaction, in honor of its discoverer.…”

Section: Introductionmentioning

confidence: 99%

MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions

Basu

Mapa

Gopinath

et al. 2006

Journal of Catalysis

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Section: Introductionmentioning

confidence: 99%

MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions

Basu

Mapa

Gopinath

et al. 2006

Journal of Catalysis

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“…2, the optimized catalyst system was applied on a technical scale to an improved total synthesis of (R)-HPB ester, key intermediate for the so-called PRIL family of ACE inhibitors [8,9] as well as related chiral building blocks [10]. In this case an a,c-diketo ester was used as starting material which resulted in slightly lower enantioselectivities compared to a-keto esters but since the keto hydroxy esters could be recrystallized, products with high optical purity were obtained.…”

Section: Heterogeneous Hydrogenation: Revival Of An Old Technologymentioning

confidence: 99%

The Development and Application of Industrially Viable Catalysts for the Selective Hydrogenation of Complex Molecules

Blaser¹

2010

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The catalysis group of Solvias has its roots in the Central Research Laboratories of Ciba-Geigy. Since the early eighties its research was focused on three areas of catalytic technology: heterogeneous hydrogenation, coupling catalysis and enantioselective homogeneous hydrogenation. Today, these are still the catalytic methods with the greatest potential for the fine chemicals industry. In this overview we will briefly describe how two of these methods, namely heterogeneous hydrogenation and enantioselective homogeneous hydrogenation have been developed further and applied in technical processes since the spin-off of Solvias in 1999. Additionally, a discussion of which strategies were successful and what the most important results have been in the first decade of Solvias' existence will follow.

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“…R-HPBA can be produced from OPBA using chemical, microbial (Yun et al, 2005), or enzymatic transformation methods. In the presence of cinchona modified Pt catalyst, the highest enantiomeric efficiency obtained for 2-oxo-4 phenylbutyric acid ethyl ester was 86% (Studer et al, 2000). Among them, biotransformation with redox enzymes has a better application prospect because it gives higher enantiomeric purity and product yield (Kim and Kim, 1991).…”

Section: Introductionmentioning

confidence: 98%

Biotransformation ofR-2-hydroxy-4-phenylbutyric acid byD-lactate dehydrogenase andCandida boidinii cells containing formate dehydrogenase coimmobilized in a fibrous bed bioreactor

Bai

Yang

2005

Biotechnol. Bioeng.

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R-2-hydroxy-4-phenylbutyric acid (R-HPBA) is an important intermediate in the manufacture of angiotensin converting enzyme inhibitors. In this work, a recombinant D-lactate dehydrogenase (LDH) was used to transform 2-oxo-4-phenylbutyric acid (OPBA) to R-HPBA, with concomitant oxidation of beta-nicotinamide adenine dinucleotide (NADH) to NAD(+). The cofactor NADH was regenerated by formate dehydrogenase (FDH) present in whole cells of Candida boidinii, which were pre-treated with toluene to make them permeable. The whole cells used in the process were more stable and easier to prepare as compared with the isolated FDH from the cells. Kinetic study showed that the reaction rate was dependent on the concentration of cofactor, NAD(+), and that both R-HPBA and OPBA inhibited the reaction. A novel method for co-immobilization of whole cells and LDH enzyme on cotton cloth was developed using polyethyleneimine (PEI), which induced the formation of PEI-enzyme-cell aggregates and their adsorption onto cotton cloth, leading to multilayer co-immobilization of cells and enzyme with high loading (0.5 g cell and 8 mg LDH per gram of cotton cloth) and activity yield ( > 95%). A fibrous bed bioreactor with co-immobilized cells and enzyme on the cotton cloth was then evaluated for R-HPBA production in fed-batch and repeated batch modes, which gave relatively stable reactor productivity of 9 g/L . h and product yield of 0.95 mol/mol OPBA when the concentrations of OPBA and R-HPBA were less than 10 g/L.

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Enantio- and chemoselective reduction of 2,4-diketo acid derivatives with cinchona modified Pt-catalyst—Synthesis of (R)-2-hydroxy-4-phenylbutyric acid ethyl ester

Cited by 44 publications

References 10 publications

MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions

MCM-41-supported platinum carbonyl cluster-derived catalysts for asymmetric and nonasymmetric hydrogenation reactions

The Development and Application of Industrially Viable Catalysts for the Selective Hydrogenation of Complex Molecules

Biotransformation ofR-2-hydroxy-4-phenylbutyric acid byD-lactate dehydrogenase andCandida boidinii cells containing formate dehydrogenase coimmobilized in a fibrous bed bioreactor

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