Enantioselective liquid–liquid extraction of (R,S)-phenylglycinol using a bisnaphthyl phosphoric acid derivative as chiral extractant

Schuur, Boelo; Verkuijl, Bjv; Bokhove, J Jeroen; Minnaard, Adriaan J.; Vries, Johannes G. de; Heeres, Hero J.; Feringa, BL Ben

doi:10.1016/j.tet.2010.11.001

Cited by 38 publications

(29 citation statements)

References 43 publications

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“…29,[47][48][49] The most important difference between the two mechanisms is when the homogeneous ligand addition mechanism applies. 29,[47][48][49] The most important difference between the two mechanisms is when the homogeneous ligand addition mechanism applies.…”

Section: Definitions and Extraction Mechanismsmentioning

confidence: 99%

Selector Screening for Enantioseparation of dl‐α‐Methyl Phenylglycine Amide by Liquid–Liquid Extraction

et al. 2014

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Enantioseparation through liquid extraction technology is an emerging field, e.g., enantioseparations of amino acids (and derivatives thereof), amino alcohols, amines, and carboxylic acids have been reported. Often, when a new selector is developed, the versatility of substrate scope is investigated. From an industrial point of view, the problem is typically approached the other way around, and for a target racemate, a selector needs to be found in order to accomplish the desired enantioseparation. This study presents such a screening approach for the separation of the enantiomers of DL-α-methyl phenylglycine amide (DL-α-MPGA), a model amide racemate with high industrial relevance. Chiral selectors that were reported for other classes of racemates were investigated, i.e., several macrocyclic selectors and Pd-BINAP complexes. It appeared very challenging to obtain both high extraction yields and good enantioselectivity for most selectors, but Pd-BINAP-based selectors performed well, with enantioselectivities up to 7.4 with an extraction yield of the desired enantiomer of 95.8%. These high enantioselectivities were obtained using dichloromethane as solvent. Using less volatile chlorobenzene or 1-chloropentane, reasonable selectivities of up to 1.7 were measured, making these the best alternative solvents for dichloromethane.

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Section: Definitions and Extraction Mechanismsmentioning

confidence: 99%

Selector Screening for Enantioseparation of dl‐α‐Methyl Phenylglycine Amide by Liquid–Liquid Extraction

et al. 2014

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show abstract

“…In this paper, we report a new method using enantioselective liquid-liquid extraction (ELLE) [13][14][15] in centrifugal contactor separator, which has excellent throughput/hold-up ratio, and good mass transfer characteristics due to fast mixing and separation [16][17][18]. As we all known, multistage extraction can give much higher efficiency than the single-stage.…”

Section: Introductionmentioning

confidence: 99%

Optimization study on continuous separation of equol enantiomers using enantioselective liquid–liquid extraction in centrifugal contactor separators

Tang

Wang

Zhang

et al. 2016

Process Biochemistry

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“…Two different approaches including asymmetric synthesis and enantioseparation of racemates have been well established to produce enantiopure compounds [2]. Among enantioseparation methods, enantioselective liquid-liquid extraction (ELLE) is considered to be a promising process because of its ease of scaling up [3]. Furthermore, another strength of ELLE is that a very high selectivity is not required, but with a moderate selectivity using a multistage process high purity can still be obtained.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective extraction of phenylsuccinic acid in aqueous two-phase systems based on acetone and β -cyclodextrin derivative: Modeling and optimization through response surface methodology

Wang

Liu

Rong

et al. 2016

Journal of Chromatography A

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Enantioselective liquid–liquid extraction of (R,S)-phenylglycinol using a bisnaphthyl phosphoric acid derivative as chiral extractant

Cited by 38 publications

References 43 publications

Selector Screening for Enantioseparation of dl‐α‐Methyl Phenylglycine Amide by Liquid–Liquid Extraction

Selector Screening for Enantioseparation of dl‐α‐Methyl Phenylglycine Amide by Liquid–Liquid Extraction

Optimization study on continuous separation of equol enantiomers using enantioselective liquid–liquid extraction in centrifugal contactor separators

Enantioselective extraction of phenylsuccinic acid in aqueous two-phase systems based on acetone and β -cyclodextrin derivative: Modeling and optimization through response surface methodology

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