Chen I-Ting, Lin Hsuan, Han Jeng-Liang
Department of Chemistry, National Chung Hsing University, Taichung 40227, Taiwan.
J Org Chem. 2025 May 30;90(21):7125-7133. doi: 10.1021/acs.joc.5c00443. Epub 2025 May 15.
An organocatalytic cascade reaction of 2-ethylidene 1,3-indandiones and isatylidene-malononitriles has been achieved using quinine as the catalyst. The unexpected vinylogous Michael addition at the β position of isatylidene-malononitriles, followed by aldol cyclization, 1,2-addition of alkoxide to nitrile, and [1,3]-O-to-N rearrangement, leads to the generation of unique spiro-bridged heterocyclic compounds containing amide, indanone, and oxindole moieties in good to excellent yields with high diastereoselectivity.
以奎宁为催化剂，实现了2-亚乙基-1,3-茚二酮与异亚苄基丙二腈的有机催化串联反应。异亚苄基丙二腈β位意外发生的插烯型迈克尔加成反应，随后进行羟醛环化、醇盐对腈的1,2-加成以及[1,3]-O到N的重排，生成了具有酰胺、茚满酮和氧化吲哚部分的独特螺桥杂环化合物，产率良好至优异，非对映选择性高。
