Chiral Brønsted-Acid-Catalyzed Asymmetric Oxidation of Sulfenamide by Using H2O2: A Versatile Access to Sulfinamide and Sulfoxide with High Enantioselectivity

Herein, we describe an example of catalytic asymmetric synthesis of sulfinamides. Aromatic sulfenamides were chosen as useful substrates, because of the indispensable N–H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. H2O2 (35%) was used as the terminal oxidant for pr...

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Bibliographic Details
Published in:ACS catalysis 2019-02, Vol.9 (2), p.1525-1530
Main Authors: Ma, Long-jun, Chen, Shu-sen, Li, Guang-xun, Zhu, Jin, Wang, Qi-wei, Tang, Zhuo
Format: Article
Language:English
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Summary:Herein, we describe an example of catalytic asymmetric synthesis of sulfinamides. Aromatic sulfenamides were chosen as useful substrates, because of the indispensable N–H bond, which could form an efficient hydrogen bond with chiral phosphoric acid. H2O2 (35%) was used as the terminal oxidant for preparation of sulfinamides in high yields and enantioselectivities, which could be easily derivatized to sulfoxides and other sulfinamides without loss of the enantioselectivity.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b04850