Sung Dan-Bi, Lee Jong Seok
Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, Busan 49111, Republic of Korea.
Department of Marine Technology & Convergence Engineering, Korea University of Science and Technology, Daejeon 34113, Republic of Korea.
Org Lett. 2023 Oct 6;25(39):7110-7114. doi: 10.1021/acs.orglett.3c02536. Epub 2023 Sep 8.
Herein, we describe a gold(I)-catalyzed intermolecular formal [2 + 2 + 2] cycloaddition of a carbonyl compound and a propiolate. A series of highly substituted 2-pyrans are accessed regioselectively from acyclic and cyclic ketones and aldehydes with various substituted propiolates using PhPAuCl (0.1-1 mol %) with two distinct metal triflate additives [0.75-7.5 mol %; In(OTf)/Cu(OTf) for ketones, Bi(OTf)/Hf(OTf) for aldehydes]. This method should provide an opportunity for further development of synthetic access to other heterocyclic compounds.
在此，我们描述了一种金（I）催化的羰基化合物与丙炔酸酯的分子间形式上的[2 + 2 + 2]环加成反应。使用PhPAuCl（0.1 - 1 mol%）与两种不同的金属三氟甲磺酸盐添加剂[0.75 - 7.5 mol%；酮用In(OTf)/Cu(OTf)，醛用Bi(OTf)/Hf(OTf)]，从无环和环状酮以及醛与各种取代丙炔酸酯中区域选择性地获得了一系列高度取代的2 - 吡喃。该方法应为进一步开发合成其他杂环化合物的途径提供机会。
