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Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitution of C3-Substituted 2-Indolylmethanols with Azlactones
Synthesis ( IF 2.6 ) Pub Date : 2017-10-12 , DOI: 10.1055/s-0036-1590929
Guang-Jian Mei , Feng Shi , Chen-Yu Bian , Dan Li , Qian Shi

Abstract

An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.

An efficient dehydrative nucleophilic substitution reaction of C3-substituted2-indolylmethanols with azlactones has been established. In the whole process, Brønsted acid was supposed to activate two substrates simultaneously. A series of structurally diversified indole derivatives were obtained in generally good yields and high diastereoselectivities (up to 86% yield, >95:5 dr). This protocol not only provides a new strategy for the direct synthesis of structurally diversified indole derivatives, but also enriches the chemistry of 2-indolylmethanols via dehydrative substitution reaction.



中文翻译:

布朗斯台德酸催化的C3取代的2-吲哚基甲醇与Az内酯的脱水亲核取代

摘要

已经建立了C3-取代的2-吲哚基甲醇与ethanol内酯的有效的脱水亲核取代反应。在整个过程中,布朗斯台德酸应同时激活两种底物。通常以良好的产率和高的非对映选择性(高达86%的产率,> 95:5 dr)获得一系列结构上多样化的吲哚衍生物。该方案不仅为直接合成结构多样化的吲哚衍生物提供了新的策略,而且通过脱水取代反应丰富了2-吲哚基甲醇的化学反应。

已经建立了C3-取代的2-吲哚基甲醇与ethanol内酯的有效的脱水亲核取代反应。在整个过程中,布朗斯台德酸应同时激活两种底物。通常以良好的产率和高的非对映选择性(高达86%的产率,> 95:5 dr)获得一系列结构上多样化的吲哚衍生物。该方案不仅为直接合成结构多样化的吲哚衍生物提供了新的策略,而且通过脱水取代反应丰富了2-吲哚基甲醇的化学反应。

更新日期:2017-10-12
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