新型手性吲哚酮类螺环化合物的合成与表征

Synthesis and Characterization of Novel Chiral Spirooxindoles

以靛红和丙二腈为原料,通过Knoevenagel缩合反应生成2-(1-取代-2-氧代吲哚-3-亚甲基)丙二腈,然后其与4-氯代乙酰乙酸乙酯在有机小分子催化剂作用下发生Michael/Cyclization串联反应,获得了标题化合物。并且进行了催化剂、溶剂和温度的筛选,发现奎宁为最优的催化剂,在室温下,以甲苯为溶剂,反应获得了最好的收率(97%)和对映选择性(e.e.99%)。产物的结构经1HNMR、13CNMR、HRMS确证。

With isatin and malononitrile as raw material, reactedby Knoevenagel condensation reaction, isatylidenemalononitriles were synthesized. Then,a cascade Miehael/eyclization reaction between isatylidenemalononitriles and 4-ehloro-3-oxobutanoate has been developed and four multieyelic spirooxindoles were prepared. A series of organic catalyst,solvent and temperature were evaluated and quinine was identified as the best catalyst for the transformation. With toluene as solvent,a number of multicyelic spirooxindoles were obtained in good yields and enantio-selectivities（ up to 97% yield,99% ee） at room temperature. The structure of the products were confirmed by ^1HNMR,^13CNMR and HRMS.