Azlactone Rings: Uniting Tradition and Innovation in Synthesis

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-28 DOI:10.1039/d5qo00657k

Marcelo H. R. Carvalho, Geovana F. Vargas, João P. R. S. Ribeiro, Pedro P. de Castro, Giovanni Wilson Amarante

引用次数: 0

Abstract

Azlactones, also known as oxazolones, are a class of heterocyclic compounds with significant relevance in the synthesis of non-natural amino acids and their derivatives. Their reactivity stems from the presence of both pro-nucleophilic and electrophilic sites, making them highly versatile and enabling a diversity of transformations. In recent years, numerous synthetic strategies utilizing azlactones as key substrates have been developed, encompassing photochemical reactions, cycloadditions, conjugate additions, and dynamic kinetic resolutions. Particular emphasis has been placed on transition-metal catalysis and organocatalyzed processes, which offer precise control over stereo- and/or regioselectivity. This review offers a comprehensive perspective on recent advances in azlactone chemistry, highlighting key reaction mechanisms and activation modes through a variety of examples.

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氮唑内酯环：传统与创新的结合

氮唑内酯，又称恶唑酮类化合物，是一类杂环化合物，在非天然氨基酸及其衍生物的合成中具有重要意义。它们的反应性源于亲核位点和亲电位点的存在，使它们具有高度的通用性，并能够进行多种转化。近年来，以氮唑内酯为主要底物的合成策略得到了发展，包括光化学反应、环加成、共轭加成和动态动力学分解。特别强调的是过渡金属催化和有机催化过程，它们提供对立体和/或区域选择性的精确控制。本文综述了近年来氮杂内酯化学的研究进展，通过实例介绍了氮杂内酯的主要反应机理和激活方式。

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.