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Selector Screening for Enantioseparation of Dl-Alpha-Methyl Phenylglycine Amide by Liquid-Liquid Extraction

Selector Screening for Enantioseparation of Dl-Alpha-Methyl Phenylglycine Amide by Liquid-Liquid Extraction, Boelo Schuur, Marek Blahusiak, Caecilia R. Vitasari, Michal Gramblicka, Andre B. De Haan, and Ton J. Visser. Chirality 2015, 27  (2), 123–130.

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Abstract

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--methyl phenylglycine amide (dl--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. Chirality 27:123-130, 2015. (c) 2014 Wiley Periodicals, Inc.

BibTeX

@article{ ISI:000349120400005,
Author = {Schuur, Boelo and Blahusiak, Marek and Vitasari, Caecilia R. and Gramblicka, Michal and De Haan, Andre B. and Visser, Ton J.},
Title = {Selector Screening for Enantioseparation of Dl-Alpha-Methyl Phenylglycine Amide by Liquid-Liquid Extraction},
Journal = {Chirality},
Year = {2015},
Volume = {27},
Number = {2},
Pages = {123-130},
Month = {},
Abstract = {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--methyl phenylglycine amide (dl--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. Chirality 27:123-130, 2015. (c) 2014 Wiley Periodicals, Inc.},
DOI = {10.1002/chir.22400},
ISSN = {0899-0042},
EISSN = {1520-636X},
Unique-ID = {ISI:000349120400005},
}

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