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3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis
Authors:Izumi Sakamoto  Kazuya Iwaoka  Yuta Kawada  Takanori Naito  Kazuyoshi Makida  Yuki Takeuchi  Takeshi Nishii  Mitsuyo Horikawa  Hiroto Kaku  Tetsuto Tsunoda
Institution:Faculty of Pharmaceutical and Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima City, Tokushima, 770-8514, Japan
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.
Keywords:Amines  Mitsunobu reaction  Phosphorane  Protecting group  Sulphonamide
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