Ring-Opening Reactions of the N-4-Nosyl Hough–Richardson Aziridine with Nitrogen Nucleophiles

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• 作者：Tomáš Ručil ; Zdeněk Trávníček ; Petr Cankař
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：82
• 期：1
• 页码：723-730
• 全文大小：415K
• ISSN：1520-6904

文摘

Dinosylated α-d-glucopyranoside was directly transformed into α-d-altropyranosides via in situ formed N-4-nosyl Hough–Richardson aziridine with nitrogen nucleophiles under mild conditions in fair to excellent yields. The scope of the aziridine ring-opening reaction was substantially broadened contrary to the conventional methods introducing solely the azide anion at high temperatures. If necessary, the N-4-nosyl Hough–Richardson aziridine can be isolated by filtration in a very good yield and high purity.