High-efficiency and minimum-waste continuous kinetic resolution of racemic alcohols by using lipase in supercritical carbon dioxide

Matsuda, Tomoko; Watanabe, Kazunori; Harada, Tadao; Nakamura, Kaoru; Arita, Yoshitaka; Misumi, Yukihiro; Ichikawa, Shinichiro; Ikariya, Takao

doi:10.1039/b406882c

Cited by 55 publications

(34 citation statements)

References 19 publications

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“…SCHEME 1. 22 Matsuda et al applied the same fl ow methodology reported by Iborra et al [164] , but did not use IL to immobilize C. antarctica Novozym 435 [165] . The KR of racemic 1 -phenylethanol was conducted with this technology for more than 3 days of operation under supercritical condition (12.9 -13 MPa of CO 2 at 42 ° C) and resulting in quantitative transformation of 221 g to ( S ) -1 -phenylethanol with 99% ee and ( R ) -(1 -phenylethyl) acetate with 99% ee using 1.73 g of the immobilized enzyme.…”

Section: Enzymesmentioning

confidence: 99%

Recyclable Stereoselective Catalysts

Monteiro¹,

Trindade²,

Góis

et al. 2011

Catalytic Methods in Asymmetric Synthesis

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Section: Enzymesmentioning

confidence: 99%

Recyclable Stereoselective Catalysts

Monteiro¹,

Trindade²,

Góis

et al. 2011

Catalytic Methods in Asymmetric Synthesis

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“…[5] Also, product recovery is facile by simple depressurisation of the reaction mixture. In addition, when combined with a fixed catalyst bed SCFs can also be used in continuous flow regimes which are highly efficient [6] and often favoured by industry. [7] Catalytic asymmetric hydrogenation reactions for the production of enantio-enriched and enantio-pure compounds have also received significant interest over the past two decades.…”

Section: Introductionmentioning

confidence: 99%

Continuous Asymmetric Hydrogenation in Supercritical Carbon Dioxide using an Immobilised Homogeneous Catalyst

et al. 2006

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Continuous flow supercritical carbon dioxide (scCO 2 ) has previously been shown (P. Stephenson, P. Licence, S. K. Ross, M. Poliakoff, Green Chem. 2004, 6, 521) to be a viable medium for conducting continuous asymmetric hydrogenation when it is combined with an appropriate enantioselective catalyst. Here we examine the use of a composite catalyst immobilisation system modified with several different types of asymmetric bisphosphine ligands in continuous flow scCO 2 . In particular, proprietary ligands from Solvias AG were found to be the most successful, with Josiphos 001 improving the enantiomeric excess (ee) to> 80 % in the asymmetric hydrogenation of dimethyl itaconate (DMIT); this ee is higher than that reported for the batch hydrogenation of DMIT using a homogeneous catalyst fully dissolved in scCO 2 (S. Lange, A. Brinkmann, P. Trautner, K. Woelk, J. Bargon, W. Leitner, Chirality 2000, 12, 450).

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“…The greatest difference between continuous-flow and batch modes can be measured by productivity (r). Productivity is a parameter that also considers the quantity of biocatalyst, measuring how much product can be obtained in 1 min ), f is the flow rate (mL min -1 ), n P is the amount of product (µmol), t is time (min) and m e is the amount of enzyme (g) [35].…”

Section: Enzymatic Kinetic Resolution (Ekr) Reactionsmentioning

confidence: 99%

“…In this context, in order to evaluate the differences between transesterification by acylation and deacylation reactions under continuous-flow conditions, a series of well-known Novozym 435® substrates [34][35][36][37][38][39][40][41][42][43], composed by benzylic and aliphatic alcohols and their respective esters were evaluated both in batch and continuous-flow modes. Finally, a multigram scale reaction was performed to validate our analytical investigation.…”

mentioning

confidence: 99%

Biocatalysis in continuous-flow mode: A case-study in the enzymatic kinetic resolution of secondary alcohols via acylation and deacylation reactions mediated by Novozym 435®

Thomas¹,

Burich²,

Bandeira³

et al. 2017

Biocatalysis

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Enzymatic kinetic resolution reactions are a well-established way to achieve optically active compounds. When enzymatic reactions are combined to continuous-flow methodologies, other benefits are added, including reproducibility, optimized energy use, minimized waste generation, among others. In this context, we herein report a case study involving lipase-mediated transesterification by acylation and deacylation reactions of secondary alcohols/esters in batch and continuous-flow modes. Acylation reactions were performed with high values of enantiomeric excess (72 up to >99%) and enantioselectivity (E > 200) for both batch and continuous-flow modes. On the other hand, for deacylation reactions using n-butanol as nucleophile, enatiomeric excess ranged between 38 to >99% and E from 6 to >200 were observed for batch mode. For deacylation reactions in continuous-flow mode, results were disappointing, as in some cases, very low or no conversion was observed. Enantiomeric excess ranged from 16 to >99% and enantioselectivity from 5 to >200 were observed. In terms of productivity, continuous-flow mode reactions were superior in both strategies (acylation: r from 1.1 up to 18.1-fold higher, deacylation: 2.8 up to 7.4- fold higher in continuous-flow than in batch mode).

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High-efficiency and minimum-waste continuous kinetic resolution of racemic alcohols by using lipase in supercritical carbon dioxide

Cited by 55 publications

References 19 publications

Recyclable Stereoselective Catalysts

Recyclable Stereoselective Catalysts

Continuous Asymmetric Hydrogenation in Supercritical Carbon Dioxide using an Immobilised Homogeneous Catalyst

Biocatalysis in continuous-flow mode: A case-study in the enzymatic kinetic resolution of secondary alcohols via acylation and deacylation reactions mediated by Novozym 435®

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