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Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair
Author(s) -
Ye Xinyi,
Moeljadi Adhitya Mangala Putra,
Chin Kek Foo,
Hirao Hajime,
Zong Lili,
Tan ChoonHong
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601574
Subject(s) - enantioselective synthesis , catalysis , chemistry , tungstate , raman spectroscopy , lansoprazole , combinatorial chemistry , organic chemistry , physics , optics , medicine , helicobacter pylori
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 H 2 O 2 , 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.