3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis |
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Authors: | Izumi Sakamoto Kazuya Iwaoka Yuta Kawada Takanori Naito Kazuyoshi Makida Yuki Takeuchi Takeshi Nishii Mitsuyo Horikawa Hiroto Kaku Tetsuto Tsunoda |
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Affiliation: | Faculty of Pharmaceutical and Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima City, Tokushima, 770-8514, Japan |
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Abstract: | 3,3-Dimethoxypropylsulfonyl (Dimps) chloride was prepared and used as a new versatile sulfonating agent for ammonia, primary and secondary amines to afford corresponding Dimps-amides in excellent yields. The resulting N-nonsubstituted and N-monosubstituted Dimps-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions. The Dimps group was removed by treatment in aqueous solution under acidic followed by basic conditions. Furthermore, epilachnene, the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized utilizing this Dimps methodology in short steps. |
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Keywords: | Amines Mitsunobu reaction Phosphorane Protecting group Sulphonamide |
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