Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Organocatalytic Mannich-Type Reactions of Cyclic N-Sulfimines with Trimethylsiloxyfuran and Pyrazolin-5-one

  • Lee, Jiseon (Department of Chemistry, Kyonggi University) ;
  • Kim, Sung-Gon (Department of Chemistry, Kyonggi University)
  • Received : 2019.05.16
  • Accepted : 2019.06.07
  • Published : 2019.10.20
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Abstract

Mannich-type reactions of cyclic N-sulfimines with 2-trimethylsiloxyfuran and pyrazolin-5-one have been developed using phosphoric acid (PA) as an organocatalyst. 2-Trimethylsiloxyfuran underwent a vinylogous Mannich-type reaction with cyclic N-sulfimines in the presence of the PA catalyst to give sulfamidate ${\gamma}$-butenolides in good yields and with high diastereoselectivities (up to 90% yield and 7:1 dr). In addition, the reaction between pyrazolin-5-one and a diverse range of cyclic N-sulfimines provided access to sulfamidates in good to high yields (up to 94% yield).

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References

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