Asymmetric Mannich Reaction of Isatin-Based Ketimines with α-Diazomethylphosphonates Catalyzed by Chiral Silver Phosphate

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• 作者：Jing Chen ; Xiaojing Wen ; Yan Wang ; Fei Du ; Liu Cai ; Yungui Peng
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4336-4339
• 全文大小：380K
• 年卷期：0
• ISSN：1523-7052

文摘

An efficient asymmetric Mannich reaction of isatin-based ketimines with α-diazomethylphosphonates has been developed using a chiral binaphthanol-derived silver phosphate as the catalyst. This reaction allowed the construction of a series of chiral oxindoles bearing a quaternary stereocenter and amino group at the C3 position with up to 95% yields and 99% ee. Those products could be further transformed into promising densely functionalized compounds by merging of the oxindole and β-aminophosphonate.