Organocatalytic asymmetric synthesis of axially and centrally chiral heterotriarylmethanes by a Friedel-Crafts reaction.

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-05-08 DOI:10.1039/d5ob00532a

Yang Min, Hanxiao Shen, Shaoying Huang, Haorui Gu, Xufeng Lin

引用次数: 0

Abstract

A highly enantioselective Friedel-Crafts reaction between C2-unsubstituted naphthyl-indoles and racemic 3-methylated-3H-pyrrolides catalyzed by chiral phosphoric acids has been developed. This reaction provides an efficient and facile route to a series of heterotricyclic triarylmethanes containing axially chiral naphthyl-indole and centrally chiral pyrrole moieties under mild conditions. Moreover, biological evaluation discovered one of these products with promising antitumor activity, and demonstrates its potential application in medicinal chemistry.

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用Friedel-Crafts反应有机催化不对称合成轴手性和中心手性杂三芳基甲烷。

研究了手性磷酸催化的2-未取代萘吲哚与3-甲基化3h -外消旋吡咯烷的高度对映选择性Friedel-Crafts反应。该反应为在温和条件下合成一系列含轴手性萘吲哚和中心手性吡咯的杂三环三芳基甲烷提供了一条高效、简便的途径。生物评价发现其中一种具有良好的抗肿瘤活性，并在药物化学方面具有潜在的应用前景。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.