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金属催化一步合成:迈向多步杂环和氨基酸衍生物形成的直接替代方法。

Metal-catalyzed one-step synthesis: towards direct alternatives to multistep heterocycle and amino acid derivative formation.

作者信息

Arndtsen Bruce A

机构信息

Department of Chemistry, McGill University, 801 Sherbrooke St. W. Montreal, QC H3A 2K6, Canada.

出版信息

Chemistry. 2009;15(2):302-13. doi: 10.1002/chem.200800767.

Abstract

The growing understanding of transition-metal catalysis has provided the opportunity to design reactions that convert simple, readily available building blocks in one step into an array of biologically relevant products. Described herein is the application of this approach to the construction of various biologically relevant products, including pyrroles, imidazoles, beta-lactams, oxazoles, alpha-amino acids, propargyl amides, functionalized pyridines, and others. These catalytic reactions rely upon several synthetic operations occurring in sequence, in which the reactivity of transition-metal complexes both activates basic building blocks towards reaction, and controls how multiple versions of these substrates come together. Overall, this allows the synthesis of each these products in one step, in high yield, with minimal waste, and with straightforward access to product diversity.

摘要

对过渡金属催化作用日益深入的理解,为设计反应提供了契机,这些反应能够将简单易得的基础原料一步转化为一系列具有生物学相关性的产物。本文描述了这种方法在构建各种具有生物学相关性产物中的应用,包括吡咯、咪唑、β-内酰胺、恶唑、α-氨基酸、炔丙基酰胺、功能化吡啶等。这些催化反应依赖于一系列依次发生的合成操作,其中过渡金属配合物的反应活性既能激活基础原料以促进反应,又能控制这些底物的多个变体如何结合在一起。总体而言,这使得能够一步合成这些产物中的每一种,产率高,浪费少,并且能够直接实现产物多样性。

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