Cascade approach for synthesis of R-1-phenyl ethyl acetate from acetophenone: Effect of support

Mäki‐Arvela, Päivi; Sahin, Serap; Kumar, Narendra; Heikkilä, Teemu; Lehto, Vesa‐Pekka; Salmi, Tapio; Murzin, Dmitry Yu.

doi:10.1016/j.molcata.2008.01.032

Cited by 24 publications

(22 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…213 By a similar approach, prochiral ketones were transformed into acylated alcohols through chemo-enzymatic heterogeneous catalytic cascade reactions using supported Pd catalysts in the initial hydrogenation step. 214 These reactions, previously carried out using homogeneous hydrogenation catalysts, 215,216 were studied in more detail than the above presented one-pot reaction of ketoximes. In most of these studies, acetophenone 33a was transformed into (R)-1-phenylethylacetate (176) by hydrogenation using supported Pd catalysts to produce racemic 1-phenylethanol (175) followed by acylation with ethyl acetate, applying the immobilized CALB (Novozym-435) catalyst.…”

Section: View Article Onlinementioning

confidence: 99%

“…In most of these studies, acetophenone 33a was transformed into (R)-1-phenylethylacetate (176) by hydrogenation using supported Pd catalysts to produce racemic 1-phenylethanol (175) followed by acylation with ethyl acetate, applying the immobilized CALB (Novozym-435) catalyst. 214,[217][218][219][220][221] In contrast to the one-pot reaction of ketoximes, in the transformation of 33a it was shown that the Pd catalyst was not efficient in the racemization step. Although optically pure 176 was obtained, the selectivity of the product did not exceeded 50%.…”

Section: View Article Onlinementioning

confidence: 99%

“…Moreover, based on results obtained using different supports, it was concluded that by-products decreased the activity of both the metal and the enzyme. 214,217,218 The sequential continuous-flow hydrogenation of 33a over Pd/SiO 2 -Al 2 O 3 and KR of 175 by immobilized CALB or crosslinked enzyme aggregates was carried out in supercritical CO 2 using consecutive reactors. 219 Later, in order to catalyse the racemization of the unreacted (S)-175, supported Ru catalyst was also introduced in the batch system, which in the absence of Pd did not promote the hydrogenation of 33a.…”

Section: View Article Onlinementioning

confidence: 99%

See 2 more Smart Citations

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

View full text Add to dashboard Cite

The preparation of optically pure fine chemicals is among the most important and challenging tasks met by organic chemists. Recently, significant efforts have been focused on the development of green and sustainable procedures for the synthesis of these high value-added compounds. Asymmetric heterogeneous catalysis has provided efficient solutions to these challenges. The application of heterogeneous chiral catalysts in one-pot processes combines the advantages of use of these materials with time, material, and energy savings associated with cascade or sequential procedures. This review surveys these asymmetric onepot reactions reported until July 2017, in which a heterogeneous chemical catalyst has been applied either as a single multifunctional catalyst or in combination with a second catalytically active material. These processes include one-pot procedures catalysed by carefully designed solids obtained by the immobilization of chiral metal complexes, by anchoring chiral organocatalysts, or by modifying catalytic surfaces with optically pure compounds, which may also incorporate uncatalyzed and homogeneously catalysed steps. Methods applying achiral heterogeneous catalysts in combination with soluble chiral chemical catalysts or biocatalysts are also presented. Sophisticated, finely tuned materials have been applied in most of these reactions, which have been discussed along with the main requirements necessary to perform these transformations in a one-pot manner.

show abstract

Section: View Article Onlinementioning

confidence: 99%

Section: View Article Onlinementioning

confidence: 99%

Section: View Article Onlinementioning

confidence: 99%

See 1 more Smart Citation

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

View full text Add to dashboard Cite

show abstract

“…Furthermore, typically Pd/AC catalysts exhibit acidic surface groups, such as carbonyl, carboxylic, phenolic hydroxyl, lactone and quinone groups [4]. It was recently reported that Brønsted acid sites enhance the hydrogenolysis of secondary alcohols, such as 1-phenylethanol, in the model reaction [5].…”

Section: Introductionmentioning

confidence: 99%

Effect of the carbon nanotube basicity in Pd/N-CNT catalysts on the synthesis of R-1-phenyl ethyl acetate

Sahin

Mäki‐Arvela

Tessonnier

et al. 2010

Scientific Bases for the Preparation of Heterogeneous Catalysts - Proceedings of the 10th International Symposium, Louvain-La-N

Self Cite

View full text Add to dashboard Cite

Catalytic activities of palladium catalysts supported on activated carbon and carbon nanotubes were investigated in the one-pot synthesis of R-1-phenylethyl acetate in combination with an immobilized lipase in toluene. Palladium catalysts on carbon nanotubes with nitrogen-containing surface groups were prepared by incipient wetness impregnation. The basic N-CNT support was synthesized by post-treating oxidized CNTs in gaseous NH3 at high temperature, prior to Pd addition. The basic character of the support was adjusted by controlling the temperature of the posttreatment step. The results showed that the desired product yield was enhanced over palladium catalysts with the lowest basicity.

show abstract

“…Ethyl benzene was generated in substantial amounts as (R,S)-1-phenyl ethyl alcohol is very prone to dehydration resulting in the formation of styrene. 14 The latter underwent hydrogenated to ethyl benzene in the presence of hydrogen. In addition to the change in the polarity of the reaction mixture, R-1-phenyl ethyl acetate was deacylated to ethyl benzene and at the same time acetic acid was formed.…”

Section: Introductionmentioning

confidence: 99%

Kinetic modeling of lipase‐mediated one‐pot chemo‐bio cascade synthesis of R‐1‐phenyl ethyl acetate starting from acetophenone

Sahin

Wärnå

Mäki‐Arvela

et al. 2009

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

show abstract

Cascade approach for synthesis of R-1-phenyl ethyl acetate from acetophenone: Effect of support

Cited by 24 publications

References 19 publications

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Effect of the carbon nanotube basicity in Pd/N-CNT catalysts on the synthesis of R-1-phenyl ethyl acetate

Kinetic modeling of lipase‐mediated one‐pot chemo‐bio cascade synthesis of R‐1‐phenyl ethyl acetate starting from acetophenone

Contact Info

Product

Resources

About