Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N, N′-cyclic azomethine imines
Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N, N′-cyclic azomethine imines
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DOI：
10.1039/c3cc41507d
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发表时间：
2013-01-01
影响因子：
4.9
通讯作者：
Wang, Rui
中科院分区：
文献类型：
--
作者：
Hong, Liang;Kai, Ming;Wang, Rui
合成了一种新的具有三轴手性的手性双磷酸3l，并将其用于N，N '-偶氮甲亚胺与亚甲基吲哚啉酮的1，3-偶极环加成反应，以高产率和高选择性合成了手性螺[吡唑烷-3，3'-羟吲哚].质谱实验和密度泛函理论计算研究提示我们提出了一种不同于传统磷酸催化的双氢键给体活化模式。
A new chiral bis-phosphoric acid 3l bearing triple axial chirality was synthesized and applied to effect a highly enantioselective 1,3-dipolar cycloaddition reaction between N,N'-azomethine imines and methyleneindolinones for the creation of chiral spiro[pyrazolidin-3,3'-oxindoles] in excellent yields and selectivities. MS experiment and DFT calculation studies prompted us to propose a dual H-bond donor activation mode of bis-phosphoric acid which is different from the traditional phosphoric acid catalysis.