IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v7y2016i1d10.1038_ncomms13455.html
   My bibliography  Save this article

Bisguanidinium dinuclear oxodiperoxomolybdosulfate ion pair-catalyzed enantioselective sulfoxidation

Author

Listed:
  • Lili Zong

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Chao Wang

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Adhitya Mangala Putra Moeljadi

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Xinyi Ye

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Rakesh Ganguly

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Yongxin Li

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Hajime Hirao

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Choon-Hong Tan

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

Abstract

Catalytic use of peroxomolybdate for asymmetric transformations has attracted increasing attention due to its catalytic properties and application in catalysis. Herein, we report chiral bisguanidinium dinuclear oxodiperoxomolybdosulfate [BG]2+[(μ-SO4)Mo2O2(μ-O2)2(O2)2]2− ion pair, as a catalyst for enantioselective sulfoxidation using aqueous H2O2 as the terminal oxidant. The ion pair catalyst is isolatable, stable and useful for the oxidation of a range of dialkyl sulfides. The practical utility was illustrated using a gram-scale synthesis of armodafinil, a commercial drug, with the catalyst generated in situ from 0.25 mol% of bisguanidinium and 2.5 mol% of Na2MoO4·2H2O. Structural characterization of this ion pair catalyst has been successfully achieved using single-crystal X-ray crystallography.

Suggested Citation

  • Lili Zong & Chao Wang & Adhitya Mangala Putra Moeljadi & Xinyi Ye & Rakesh Ganguly & Yongxin Li & Hajime Hirao & Choon-Hong Tan, 2016. "Bisguanidinium dinuclear oxodiperoxomolybdosulfate ion pair-catalyzed enantioselective sulfoxidation," Nature Communications, Nature, vol. 7(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13455
    DOI: 10.1038/ncomms13455
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/ncomms13455
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/ncomms13455?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Shiwei Lü & Zipeng Wang & Shifa Zhu, 2022. "Thiol-Yne click chemistry of acetylene-enabled macrocyclization," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13455. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.