Lewis酸催化Michael加成/环化级联合成螺菌吲哚衍生物的对映选择性研究。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-09-08 DOI:10.1021/acs.joc.5c01565

Fen Tan*, Zhou-Yang Xu, Zhen Li, Yao-Xin Zhang, Xiao-Qin Xiong*, Xiao-Yu He and You-Quan Zou*,

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引用次数: 0

摘要

在Mg(OTf)2催化下，建立了3-异硫氰酸酯氧吲哚与2-芳基烯-1,3-茚二酮的不对称Michael加成/环化级联反应。该转化为在温和条件下获得具有重要生物学意义的比斯皮罗[茚二酮-氧吲哚-吡咯烷基]s提供了一种高效而简洁的方法，产率从良好到优异（70-99%），具有中等到良好的立体选择性（高达99% ee和bbb95:5 d.r）。值得注意的是，生物学研究表明，合成的一种bispiro[indanedione-oxindole- pyrolidinyl]s对NCI-H460人肺癌细胞和SW-620人结肠癌细胞具有良好的细胞毒性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective Synthesis of Spirooxindole Derivatives through Lewis Acid-Catalyzed Michael Addition/Cyclization Cascade

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Enantioselective Synthesis of Spirooxindole Derivatives through Lewis Acid-Catalyzed Michael Addition/Cyclization Cascade

A Mg(OTf)₂-catalyzed asymmetric Michael addition/cyclization cascade reaction between 3-isothiocyanato oxindoles and 2-arylidene-1,3-indanediones has been developed. This transformation provides an efficient and concise approach to biologically important bispiro[indanedione-oxindole-pyrrolidinyl]s under mild conditions in good to excellent yields (70–99% yields) with moderate to good stereoselectivities (up to 99% ee and >95:5 d.r.). Notably, biological investigation reveals that one of the synthesized bispiro[indanedione-oxindole-pyrrolidinyl]s exhibits promising cytotoxicity against NCI-H460 human lung cancer and SW-620 human colon cancer cells.

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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.