Asymmetric Mannich Reaction of Isatin-Based Ketimines with α-Diazomethylphosphonates Catalyzed by Chiral Silver Phosphate
Asymmetric Mannich Reaction of Isatin-Based Ketimines with α-Diazomethylphosphonates Catalyzed by Chiral Silver Phosphate
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手性磷酸银催化靛红基酮亚胺与α-重氮甲基膦酸酯的不对称曼尼希反应
DOI：
10.1021/acs.orglett.6b02095
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发表时间：
2016-09-02
期刊：
影响因子：
5.2
通讯作者：
Peng, Yungui
中科院分区：
文献类型：
--
作者：
Chen, Jing;Wen, Xiaojing;Peng, Yungui
以联萘甲醇衍生的银磷酸盐为催化剂，研究了靛红酮亚胺与手性α-重氮甲基膦酸酯的不对称Mannich反应。该反应允许一系列的手性羟吲哚轴承一个四元立体中心和氨基在C3位置的建设高达95%的产率和99%ee。这些产品可以进一步转化为有前途的密集功能化的化合物合并的羟吲哚和β-氨基膦酸酯。
An efficient asymmetric Mannich reaction of isatin-based ketimines withchiral alpha-diazomethylphosphonates has been developed using a 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 beta-aminophosphonate.