Catalytic enantioselective and site-specific Friedel−Crafts alkylation of 4-aminoindoles with β,γ-alkynyl-α-ketoimines for the synthesis of C7-functionalized indoles

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-19 DOI:10.1039/d4qo01856g

Lei Yang, Xue-Man Zhang, Juan Liao, Yan-Ping Zhang, Zhen-Hua Wang, Yong You, Jian-Qiang Zhao, Wei-Cheng Yuan

引用次数: 0

Abstract

Chiral phosphoric acid-catalyzed enantioselective Friedel−Crafts alkylation of 4‑aminoindoles with β,γ-alkynyl-α-ketoimines has been developed. A range of optically pure C7-functionalized indoles bearing a quaternary α-amino acid or trifluoromethylated tetrasubstituted alkylamine motif were obtained with up to 98% yield and 99% ee. This protocol effectively incorporates the site-specific Friedel-Crafts alkylation at the C7 site of 4‑aminoindoles and regio-specific quaternary stereocenter construction at the α-position of β,γ-alkynyl-α-ketoimines, and opens a new avenue to access chiral C7-functionalized indoles.

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催化对映体选择性和位点特异性 Friedel-Crafts 烷基化 4-氨基吲哚与 β、γ-炔基-α-酮亚胺合成 C7 功能化吲哚

研究人员开发了手性磷酸催化的 4-氨基吲哚与 β、γ-炔基-α-酮亚胺的对映选择性 Friedel-Crafts 烷基化反应。获得了一系列光学纯的 C7 功能化吲哚，这些吲哚含有季α-氨基酸或三氟甲基化四取代烷基胺基团，收率高达 98%，ee 为 99%。该方案有效地结合了 4-氨基吲哚 C7 位特异性 Friedel-Crafts 烷基化反应和 β、γ-炔基-α-酮亚胺 α 位特异性四元立体中心构建反应，为获得手性 C7 功能化吲哚开辟了一条新途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.