Highly Stereoselective Recognition and Deracemization of Amino Acids by Supramolecular Self‐Assembly |
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Authors: | Dr. Soon Mog So Kimia Moozeh Dr. Alan J. Lough Prof. Jik Chin |
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Affiliation: | Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com |
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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. |
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Keywords: | amino acids molecular recognition stereoinversion stereoselectivity supramolecular self‐assembly |
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