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Highly Efficient and Robust Enantioselective Liquid–Liquid Extraction of 1,2‐Amino Alcohols utilizing VAPOL‐ and VANOL‐based Phosphoric Acid Hosts
Author(s) -
Pinxterhuis Erik B.,
Gualtierotti JeanBaptiste,
Wezenberg Sander J.,
de Vries Johannes G.,
Feringa Ben L.
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201701896
Subject(s) - enantiopure drug , enantioselective synthesis , phosphoric acid , extraction (chemistry) , combinatorial chemistry , chemistry , liquid–liquid extraction , chiral resolution , organic chemistry , catalysis , enantiomer
The large‐scale production of enantiopure compounds in a cost‐effective and environmentally friendly manner remains one of the major challenges of modern‐day chemistry. The resolution of racemates through enantioselective liquid–liquid extraction was developed as a suitable solution but has remained largely underused, owing to a lack of highly efficient and robust chiral hosts to mediate the process. This paucity of hosts can in part be attributed to a poor understanding of the underlying principles behind these processes hindering the design of more efficient selectors. A previously untested class of hosts, VAPOL and VANOL derived phosphoric acids, has been studied in depth for the efficient enantioselective liquid–liquid extraction of 1,2‐amino alcohols. A systematic investigation of extraction parameters was conducted, revealing many key interactions and DFT calculations illustrate the binding modes for the 1:1 complexes that are involved in chiral recognition. The resulting, now‐optimized, procedures are highly robust and easy to implement. They are also easily scalable, as demonstrated by U‐tube experiments.