通过化学选择性链化Michael/环化/重排序列的有机催化合成螺旋桥接杂环化合物。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI:10.1021/acs.joc.5c00443

I-Ting Chen,Hsuan Lin,Jeng-Liang Han

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引用次数: 0

摘要

以奎宁为催化剂，实现了2-乙基- 1,3-茚二酮与异亚基-丙二腈的有机催化级联反应。在异丙二烯-丙二腈的β位置意外发生的乙烯基Michael加成，接着是醛醇环化、烷氧基1,2加成和[1,3]- o- n重排，产生了独特的螺桥杂环化合物，其中含有酰胺、吲哚酮和氧化吲哚基团，收率很高，具有高非对映选择性。

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Organocatalytic Synthesis of Spiro-Bridged Heterocyclic Compounds via a Chemoselective Vinylogous Michael/Cyclization/Rearrangement Sequence.

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.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.