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http://dx.doi.org/10.5012/jkcs.2019.63.5.346

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)
Publication Information
Journal of the Korean Chemical Society / v.63, no.5, 2019 , pp. 346-351 More about this Journal
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).
Keywords
Mannich reaction; Sulfamidate; Trimethylsiloxyfuran; Pyrazolin-5-one; Phosphoric acid;
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