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- Title
Highly Stereoselective Recognition and Deracemization of Amino Acids by Supramolecular Self-Assembly.
- Authors
So, Soon Mog; Moozeh, Kimia; Lough, Alan J.; Chin, Jik
- Abstract
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.
- Subjects
STEREOSELECTIVE reactions; DERACEMIZATION; AMINO acids; SUPRAMOLECULAR chemistry; ALDEHYDES; CHIRALITY; BINAPHTHOL
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 3, p848
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201307410