通过有机催化剂介导的环丙化合成高立体和对映选择性的螺环丙基氧吲哚

IF 8.9 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chinese Chemical Letters Pub Date : 2025-02-06 DOI:10.1016/j.cclet.2025.110923

Min Liu , Di Wang , Zenghui Ye , Donghao Jiang , Bencan Tang , Yanqi Wu , Fengzhi Zhang

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引用次数: 0

摘要

螺环丙基氧吲哚广泛存在于天然产物和药用分子中。在此，我们报道了一个高度立体和对映选择性的过程，通过叔胺介导的环丙化反应，以原位Heck反应生成的3-烯基吲哚酮作为Michael受体来获得这类化合物。该反应条件温和，具有良好的对映选择性（高达98 %）和非对映选择性（高达99:1），高原子经济性和阶梯经济性，广泛的底物范围和良好的官能团耐受性。此外，这种可扩展的合成工艺为高效合成对映纯螺环丙基氧吲哚提供了一种新的策略。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Highly stereo- and enantio‑selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation

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Highly stereo- and enantio‑selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation

Spiro-cyclopropyl oxindoles are widely found in natural products and medicinal molecules. Herein, we report a highly stereo- and enantio‑selective procedure for accessing this class of compounds via tertiary amine mediated cyclopropanation of ammonium ylides with the in-situ Heck reaction-generated 3-alkenyl indolones as the Michael receptors. This reaction features mild conditions, excellent enantioselectivity (up to 98 %) and diastereoselectivity (up to 99:1), high atom- and step-economy, broad substrate scopes, and good functional group tolerance. Additionally, this scalable synthetic process could offer a novel strategy for the efficient synthesis of enantiopure spirocyclopropyl oxindoles.

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来源期刊

Chinese Chemical Letters 化学-化学综合

CiteScore

14.10

自引率

15.40%

发文量

8969

审稿时长

1.6 months

期刊介绍： Chinese Chemical Letters (CCL) (ISSN 1001-8417) was founded in July 1990. The journal publishes preliminary accounts in the whole field of chemistry, including inorganic chemistry, organic chemistry, analytical chemistry, physical chemistry, polymer chemistry, applied chemistry, etc.Chinese Chemical Letters does not accept articles previously published or scheduled to be published. To verify originality, your article may be checked by the originality detection service CrossCheck.