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One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN3: Rapid Access to Polycyclic Alkaloids

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posted on 06.08.2010, 00:00 by Yu-Ming Zhao, Peiming Gu, Yong-Qiang Tu, Hai-Jun Zhang, Qing-Wei Zhang, Chun-An Fan
A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated. The structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time. As the application of this methodology, the synthesis of polycyclic alkaloid hexahydroapoerysopine (1a) was achieved through an efficient synthetic route.