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唑酮在有机催化中的应用:老试剂的新把戏。

Oxazolones in organocatalysis, new tricks for an old reagent.

机构信息

Departament de Química Orgànica, Universitat de Barcelona, C/Martí i Franquès 1-11, 08028 Barcelona, Spain.

出版信息

Chem Asian J. 2011 Mar 1;6(3):720-34. doi: 10.1002/asia.201000636. Epub 2011 Jan 11.

Abstract

Oxazolones or azlactones are among the most-common starting materials for the synthesis of quaternary amino acids. Since the seminal works of Steglich and co-workers until the recent examples from Ooi and co-workers, azlactones have been the focus of intense research. Oxazolones are also widely used in organometallic chemistry; however, with the "renaissance" of organocatalysis, this reagent has emerged as an important starting material for a broad range of new organocatalytic asymmetric methodologies. In this Focus Review, we aim to cover all of these new organocatalytic methodologies. We begin by discussing the dynamic kinetic resolution reactions developed with azlactones. Then, we disclose the organocatalytic rearrangements. Finally, we focus on the use of oxazolones as nucleophiles in organocatalytic processes.

摘要

唑酮或内酰胺是合成季铵氨基酸最常用的起始材料之一。自 Steglich 及其同事的开创性工作到最近 Ooi 及其同事的例子,内酰胺一直是研究的焦点。唑酮也广泛用于有机金属化学;然而,随着有机催化的“复兴”,这种试剂已成为广泛的新型有机催化不对称方法的重要起始材料。在这篇重点综述中,我们旨在涵盖所有这些新的有机催化方法。我们首先讨论了用内酰胺开发的动态动力学拆分反应。然后,我们揭示了有机催化重排。最后,我们专注于唑酮作为亲核试剂在有机催化过程中的应用。

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