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Carbene-Catalyzed [4+2] Cycloaddition of Cyclobutenones and Isatins for Quick Access to Chiral Chlorine-Containing Spirocyclic δ-Lactones
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-05-02 , DOI: 10.1021/acs.joc.4c00295
Bin Liu 1 , Xian Zhou 1 , Qinqin Liu 1 , Zaihui Yang 1 , Yuanhu Mao 1 , Qing He 1 , Tianyuan Zhang 1 , Xiangkai Kong 1 , Jiquan Zhang 1 , Weike Liao 1 , Lei Tang 1
Affiliation  

Here we report a carbene-catalyzed enantio- and diastereoselective [4+2] cycloaddition reaction of cyclobutenones with isatins for the quick and efficient synthesis of spirocyclic δ-lactones bearing a chiral chlorine. A broad range of substrates with various substitution patterns proceed smoothly in this reaction, with the spirooxindole δ-lactone products afforded in generally good to excellent yields and optical purities under mild reaction conditions.

中文翻译:

卡宾催化[4+2]环丁烯酮和靛红的环加成反应快速生成手性含氯螺环δ-内酯

在这里,我们报道了卡宾催化的环丁烯酮与靛红的对映和非对映选择性[4+2]环加成反应,用于快速有效地合成带有手性氯的螺环δ-内酯。具有各种取代模式的多种底物在此反应中顺利进行,在温和的反应条件下,螺吲哚δ-内酯产物通常具有良好至优异的产率和光学纯度。
更新日期:2024-05-02
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