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Highly Stereoselective Recognition and Deracemization of Amino Acids by Supramolecular Self‐Assembly
Author(s) -
So Soon Mog,
Moozeh Kimia,
Lough Alan J.,
Chin Jik
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307410
Subject(s) - stereoselectivity , amino acid , supramolecular chemistry , chemistry , aldehyde , salt (chemistry) , stereochemistry , guanidine , chirality (physics) , combinatorial chemistry , organic chemistry , crystal structure , catalysis , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The highly stereoselective supramolecular self‐assembly of α‐amino acids with a chiral aldehyde derived from binol and a chiral guanidine derived from diphenylethylenediamine (dpen) to form the imino acid salt is reported. This system can be used to cleanly convert D ‐amino acids into L ‐amino acids or vice versa at ambient temperature. It can also be used to synthesize α‐deuterated D ‐ or L ‐amino acids. A crystal structure of the ternary complex together with DFT computation provided detailed insight into the origin of the stereoselective recognition of amino acids.