Recent developments in optical resolution

Siedlecka, Renata

doi:10.1016/j.tet.2013.05.035

Cited by 76 publications

(55 citation statements)

References 131 publications

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“…For example, the recent asymmetric synthesis of enantiomerically pure 1 [55] involves the reductive amination of the corresponding ketone using rather expensive Ellman’s chiral sulfinimide [56,57,58] as a chiral auxiliary. Accordingly, with the aim to develop an economically sound process, and drawing inspiration from the recent publications of optical resolutions of various chiral amines [59,60,61,62,63] and, in particular, patent data [64], we focused our attention on the optical resolution approach, the science of which is well understood and can be performed on an industrial scale [65,66,67,68].…”

Section: Resultsmentioning

confidence: 99%

Optical Resolution of Rimantadine

et al. 2019

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This work discloses a new procedure for the resolution of commercially available racemic rimantadine hydrochloride to enantiomerically pure (S)-rimantadine using (R)-phenoxypropionic acid as a recyclable resolving reagent. Good chemical yields, operational ease, and low-cost structure underscore the preparative value of this method for the production of enantiomerically pure rimantadine for medicinal or synthetic studies.

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Section: Resultsmentioning

confidence: 99%

Optical Resolution of Rimantadine

et al. 2019

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“…Several chemical methods are available for producing optically active chiral compounds (Siedlecka 2013;Fogassy et al 2006). However, biological approaches as biocatalysis and bioconversion are advantageous due to their high efficiency, mild reaction conditions, stereospecificity and low environmental impact (Johannes et al 2006).…”

Section: Introductionmentioning

confidence: 99%

Neat lipase-catalysed kinetic resolution of racemic 1-phenylethanol and a straightforward modelling of the reaction

Varga

Kmecz

Szécsényi

et al. 2017

Biocatalysis and Biotransformation

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Enzymatic kinetic resolution of racemic 1-phenylethanol catalyzed by immobilized Candida antarctica lipase B was investigated in a neat systems at the temperature range of 30-70°C. Synthetic triglycerides, namely glycerol triacetate and glycerol tributyrate, were applied as the esterification agents. Both esterification agents were efficient regarding to the enantioselectivity (>1000). Initial rate of reaction and the kinetic constants were influenced by the applied esterification agent significantly. A detailed modelling approach is presented and verified in the temperature range on 30-60°C for the tributyrin system.

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“…1 In the reaction of a racemic compound and the appropriate homochiral compound, the resolving agent, diastereomers are formed which can be separated due to their different chemical and physical properties. [2][3][4][5][6][7] In addition to solid solutions, enantiomeric mixtures may be divided into conglomerate or racemate-forming compounds depending on whether the formation of the corresponding homoor heterochiral associates is preferred. Approximately 80% of enantiomeric mixtures show racemate behavior.…”

Section: Introductionmentioning

confidence: 99%