Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
J Am Chem Soc. 2013 Mar 20;135(11):4167-70. doi: 10.1021/ja3110544. Epub 2013 Mar 12.
A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.
报道了一种钯催化的 1,4-加成反应，使商品化学物质 1,3-丁二烯发生反应，生成缺电子多烯产物。通过钯的 σ → π → σ 烯丙基异构化，以高区域选择性和新形成的烯烃的反式立体选择性形成两个新的碳-碳键。该方法的实用性通过成功合成 ripostatin A 缺电子三烯核心得到了突出体现。
