3-(3-indolomethyl)-oxindoles 的不对称催化简易合成，用于构建三叉类似物

IF 4.3 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemical Communications Pub Date : 2024-09-26 DOI:10.1039/d4cc03327b

Zun Yang , Zheng Jiang , Zheng Tan , Han Yu , Xiaoming Feng , Xiaohua Liu

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引用次数: 0

摘要

利用一种 N,N'-二氧/Ho(III)络合物，通过将吲哚取代的烯醇化酮酯与 3-溴-3-取代的吲哚加成，实现了 3-(3-吲哚甲基)吲哚的不对称合成。研究人员获得了多种可能具有生物活性的 3-(3-indolomethyl)羰基吲哚，其产率高，非对映和对映选择性高（产率高达 97%，对映选择性为 19:1，ee 为 98%）。此外，非对映选择性的时间依赖性逆转使得获得光学活性二元酯成为可能。该产品随后的简便转化为三叉类似物提供了一条新途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric catalytic concise synthesis of 3-(3-indolomethyl)-oxindoles for the construction of trigolute analogs†

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Asymmetric catalytic concise synthesis of 3-(3-indolomethyl)-oxindoles for the construction of trigolute analogs†

Asymmetric synthesis of 3-(3-indolomethyl)oxindoles through the addition of indole-substituted enolized ketoesters to 3-bromo-3-substituted oxindoles has been achieved using a N,N′-dioxide/Ho(iii) complex. A number of 3-(3-indolomethyl)oxindoles, which may possess biological activity, were obtained in good yields with high diastereo- and enantioselectivities (up to 97% yield, >19 : 1 dr, 98% ee). Furthermore, time-dependent reversal of diastereoselectivity enabled access to optically active diastereomers. The product followed by facile transformations gave a new route into trigolute analogs.

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来源期刊

Chemical Communications 化学-化学综合

CiteScore

8.60

自引率

4.10%

发文量

2705

审稿时长

1.4 months

期刊介绍： ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.