Chiral Phosphoric Acid Catalyzed Asymmetric Mannich Reaction of 2-Aryl-3H-indol-3-ones with α-H Diazoacetates

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-13 DOI:10.1021/acs.orglett.5c00712

Cheng Lin, Jia-Hao He, Ming-Liang Rao, Gui-Ping Yang, Wen-Jie Li, Meng Zhou, Chong Zhao, Xiao-Zhong Fu, Bin He, Yong-Long Zhao

引用次数: 0

Abstract

An asymmetric Mannich reaction between 2-aryl-3H-indol-3-ones and α-H diazoacetates catalyzed by chiral phosphoric acid was developed. This strategy achieves the effective synthesis of chiral 2,2-disubstituted indolin-3-ones bearing a quaternary stereocenter and containing a diazo group in the C2 substituent (up to >99% ee and 82% yield). To demonstrate the importance of the synthesized 2,2-disubstituted indolin-3-ones and the diversity of their diazo group reactions, we successfully achieved the relevant transformation reactions with a diazo group (such as hydroxylation, hydrogenation, intramolecular cyclization, etc.) in the C2 substituent.

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手性磷酸催化2-芳基- 3h -吲哚-3-酮与α-H重氮乙酸酯的不对称Mannich反应

研究了手性磷酸催化2-芳基- 3h -吲哚-3-酮与α-H重氮乙酸酯的不对称曼尼希反应。该策略实现了手性2,2-二取代吲哚-3-酮的有效合成，具有一个季立体中心，在C2取代基上含有重氮基团（高达99%的ee和82%的产率）。为了证明合成的2,2-二取代吲哚-3-酮的重要性及其重氮基团反应的多样性，我们成功地在C2取代基上实现了重氮基团的相关转化反应（如羟基化、氢化、分子内环化等）。

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 Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.