Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Xinyi Ye
  • Adhitya Mangala Putra Moeljadi
  • Kek Foo Chin
  • Lili Zong
  • Choon-Hong Tan

Detail(s)

Original languageEnglish
Pages (from-to)7101-7105
Journal / PublicationAngewandte Chemie - International Edition
Volume55
Issue number25
Publication statusPublished - 2016
Externally publishedYes

Abstract

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.

Research Area(s)

  • asymmetric sulfoxidation, bisguanidinium, ion-pair catalysis, lansoprazole, Raman spectroscopy

Citation Format(s)

Enantioselective Sulfoxidation Catalyzed by a Bisguanidinium Diphosphatobisperoxotungstate Ion Pair. / Ye, Xinyi; Moeljadi, Adhitya Mangala Putra; Chin, Kek Foo; Hirao, Hajime; Zong, Lili; Tan, Choon-Hong.

In: Angewandte Chemie - International Edition, Vol. 55, No. 25, 2016, p. 7101-7105.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review