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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 63, Number 5
JKCSEZ 63(5)
October 20, 2019 

Organocatalytic Mannich-Type Reactions of Cyclic N-Sulfimines with Trimethylsiloxyfuran and Pyrazolin-5-one
Jiseon Lee, Sung Gon Kim*
Mannich reaction, Sulfamidate, Trimethylsiloxyfuran, Pyrazolin-5-one, Phosphoric acid
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 γ-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 Nsulfimines provided access to sulfamidates in good to high yields (up to 94% yield).
346 - 351
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