Advancements in isocyanide based multicomponent reactions.

机译：基于异氰化物的多组分反应的进展。

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Isocyanide based multicomponent reactions, including the Ugi four-component and Passerini three-component reactions, offer chemists a powerful tool for quickly constructing complex molecules. A particular form of the Ugi reaction, in which two of the four reacting components are introduced into a single molecule, is useful for synthesizing cyclic products. Using a newly developed convertible isocyanide, known as indole isocyanide, in the Ugi reaction allowed for the mild synthesis of various pyroglutamic acids. This effort led first to a racemic total synthesis of the natural product dysibetaine. A project to achieve the stereoselective synthesis of the same natural product led to the discovery of a unique Ugi reaction. Usually a carboxylic acid is one of the four reacting components in this reaction, however in this unusual case an ester acts as the carboxylic acid component. In addition to the natural product syntheses, a detailed explanation of the scope and mechanism of the new convertible indole isocyanide is presented. Finally, we reveal a new stereoselective, Bronsted-acid catalyzed Passerini-type reaction.

机译：基于异氰化物的多组分反应，包括Ugi四组分和Passerini三组分反应，为化学家提供了快速构建复杂分子的强大工具。 Ugi反应的一种特殊形式，其中将四个反应成分中的两个引入一个分子中，可用于合成环状产物。在Ugi反应中使用新开发的可转换异氰酸酯（称为吲哚异氰酸酯）可以温和合成各种焦谷氨酸。这项努力首先导致了天然产物dysibetaine的外消旋全合成。一个实现相同天然产物立体选择性合成的项目导致了独特的Ugi反应的发现。通常，羧酸是该反应中四个反应组分之一，但是在这种不寻常的情况下，酯充当了羧酸组分。除了合成天然产物外，还对新型可转换的吲哚异氰酸酯的范围和机理进行了详细说明。最后，我们揭示了一种新的立体选择性布朗斯台德酸催化的Passerini型反应。

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Isaacson, Jerry Calhoun.;
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University of California, San Diego.;

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授予单位 University of California, San Diego.;
学科 Chemistry Organic.
学位 Ph.D.
年度 2009
页码 459 p.
总页数 459
原文格式 PDF
正文语种 eng
中图分类有机化学;
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入库时间 2022-08-17 11:38:24

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Advancements in isocyanide based multicomponent reactions.

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