期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 11, 页码 4335-4339出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914797
关键词
amino acids; enantiopurity; deracemisation; hydrogen bonds; reaction mechanisms
资金
- Natural Science and Engineering Research Council (NSERC)
- University of Toronto
- Province of Ontario
l to d conversion of unactivated alpha-amino acids was achieved by solubility-induced diastereomer transformation (SIDT). Ternary complexes of an alpha-amino acid with 3,5-dichlorosalicylaldehyde and a chiral guanidine (derived from corresponding chiral vicinal diamine) were obtained in good yield as diastereomerically pure imino acid salt complexes and were hydrolysed to obtain enantiopure alpha-amino acids. A combination of DFT computation, NMR spectroscopy, and crystal structure provide detailed insight into how two types of strong hydrogen bonds assist in rapid epimerization of the complexes that is essential for SIDT.
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