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Issue 9, 2017
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Highly efficient enantioselective liquid–liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

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Abstract

Access to enantiopure compounds on large scale in an environmentally friendly and cost-efficient manner remains one of the greatest challenges in chemistry. Resolution of racemates using enantioselective liquid–liquid extraction has great potential to meet that challenge. However, a relatively feeble understanding of the chemical principles and physical properties behind this technique has hampered the development of hosts possessing sufficient resolving power for their application to large scale processes. Herein we present, employing the previously untested SPINOL based phosphoric acids host family, an in depths study of the parameters affecting the efficiency of the resolution of amino-alcohols in the optic of further understanding the core principles behind ELLE. We have systematically investigated the dependencies of the enantioselection by parameters such as the choice of solvent, the temperature, as well as the pH and bring to light many previously unsuspected and highly intriguing interactions. Furthermore, utilizing these new insights to our advantage, we developed novel, highly efficient, extraction and resolving protocols which provide remarkable levels of enantioselectivity. It was shown that the extraction is catalytic in host by demonstrating transport in a U-tube and finally it was demonstrated how the solvent dependency could be exploited in an unprecedented triphasic resolution system.

Graphical abstract: Highly efficient enantioselective liquid–liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

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Supplementary files

Article information


Submitted
22 Jun 2017
Accepted
13 Jul 2017
First published
21 Jul 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 6409-6418
Article type
Edge Article

Highly efficient enantioselective liquid–liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

E. B. Pinxterhuis, J. Gualtierotti, H. J. Heeres, J. G. de Vries and B. L. Feringa, Chem. Sci., 2017, 8, 6409
DOI: 10.1039/C7SC02783D

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