Bisguanidinium dinuclear oxodiperoxomolybdosulfate ion pair-catalyzed enantioselective sulfoxidation

Lili Zong, Chao Wang, Adhitya Mangala Putra Moeljadi, Xinyi Ye, Rakesh Ganguly, Yongxin Li, Hajime Hirao () and Choon-Hong Tan ()
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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

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms13455

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