Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Żeromskiego 116, 90-924 Łódź, Poland.
Department of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
J Org Chem. 2020 Mar 6;85(5):2938-2944. doi: 10.1021/acs.joc.9b02530. Epub 2020 Feb 20.
In this work, the first application of 3,5-dimethyl-4-nitroisoxazole as a vinylogous pronucleophile in the allylic-allylic alkylation of Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been realized under nucleophilic catalysis conditions with dimeric cinchona alkaloids, providing excellent enantiocontrol of the process. The usefulness of the products thus obtained has been confirmed in selected chemoselective reactions. The most important one involves the transformation of the isoxazole moiety into a carboxylic acid group, thus opening access to dicarboxylic acid derivatives.
在这项工作中，首次将 3,5-二甲基-4-硝基异恶唑作为一个烯基亲核试剂应用于 Morita-Baylis-Hillman (MBH) 碳酸酯的烯丙基-烯丙基烷基化反应中。该反应在双核金鸡纳生物碱的亲核催化条件下实现，为该过程提供了极好的对映选择性控制。所得产物在一些选择性化学反应中得到了证实。其中最重要的一个涉及将异恶唑部分转化为羧酸基团，从而可以获得二羧酸衍生物。
