Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 25, Pages 7101-7105Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601574
Keywords
asymmetric sulfoxidation; bisguanidinium; ion-pair catalysis; lansoprazole; Raman spectroscopy
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Funding
- NTU [M4080946.110, M4011372.110]
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The first enantioselective tungstate-catalyzed oxidation reaction is presented. High enantioselectivities were achieved for a variety of drug-like phenyl and heterocyclic sulfides under mild conditions with H2O2, a cheap and environmentally friendly oxidant. Synthetic utility was demonstrated through the preparation of (S)-Lansoprazole, a commercial proton-pump inhibitor. The active ion-pair catalyst was identified to be bisguanidinium diphosphatobisperoxotungstate using Raman spectroscopy and computational studies.
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