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3,3′‐diaryl‐BINOL phosphoric acids as enantioselective extractants of benzylic primary amines
Author(s) -
Verkuijl Bastiaan J.V.,
de Vries Johannes G.,
Feringa Ben L.
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20834
Subject(s) - chemistry , enantioselective synthesis , phosphoric acid , primary (astronomy) , organic chemistry , combinatorial chemistry , catalysis , physics , astronomy
We report that 3,3′‐diaryl‐BINOL phosphoric acids are effective enantioselective extractants in chiral separation methods based on reactive liquid–liquid extraction. These new extractants are capable of separating racemic benzylic primary amine substrates. The effect of the nature of the substituents at the 3,3′‐positions of the host were examined as well as the structure of the substrate, together with important parameters such as the organic solvent, the pH of the aqueous phase, and the host stoichiometry. Titration of the substrate with the host was monitored by FTIR, NMR, UV–Vis, and CD spectroscopy, which provided insight into the structure of the host–guest complex involved in extraction. Chirality 2011. © 2010 Wiley‐Liss, Inc.