Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000, PR China.
Chem Commun (Camb). 2013 Aug 4;49(60):6713-5. doi: 10.1039/c3cc41507d.
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-3,30-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.
一种新型的手性双膦酸 3l 具有三重轴向手性，被合成出来并应用于氮杂亚甲胺亚胺和亚甲基吲哚啉酮之间的高对映选择性 1,3-偶极环加成反应，以优异的收率和选择性合成手性螺[吡咯烷-3,30-氧吲哚]。MS 实验和 DFT 计算研究促使我们提出了双膦酸的双重氢键供体活化模式，这与传统的磷酸催化不同。
