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Ferrocene derivatives with planar chirality and their enantioseparation by liquid-phase techniques
Electrophoresis ( IF 3.0 ) Pub Date : 2022-08-10 , DOI: 10.1002/elps.202200148
Paola Peluso 1 , Victor Mamane 2
Affiliation  

In the last decade, planar chiral ferrocenes have attracted a growing interest in several fields, particularly in asymmetric catalysis, medicinal chemistry, chiroptical spectroscopy and electrochemistry. In this frame, the access to pure or enriched enantiomers of planar chiral ferrocenes has become essential, relying on the availability of efficient asymmetric synthesis procedures and enantioseparation methods. Despite this, in enantioseparation science, these metallocenes were not comprehensively explored, and very few systematic analytical studies were reported in this field so far. On the other hand, enantioselective high-performance liquid chromatography has been frequently used by organic and organometallic chemists in order to measure the enantiomeric purity of planar chiral ferrocenes prepared by asymmetric synthesis. On these bases, this review aims to provide the reader with a comprehensive overview on the enantioseparation of planar chiral ferrocenes by discussing liquid-phase enantioseparation methods developed over time, integrating this main topic with the most relevant aspects of ferrocene chemistry. Thus, the main structural features of ferrocenes and the methods to model this class of metallocenes will be briefly summarized. In addition, planar chiral ferrocenes of applicative interest as well as the limits of asymmetric synthesis for the preparation of some classes of planar chiral ferrocenes will also be discussed with the aim to orient analytical scientists towards ‘hot topics’ and issues which are still open for accessing enantiomers of ferrocenes featured by planar chirality.

中文翻译:

具有平面手性的二茂铁衍生物及其液相技术的对映分离

在过去十年中,平面手性二茂铁在多个领域引起了越来越多的兴趣,特别是在不对称催化、药物化学、手性光谱学和电化学方面。在这个框架中,获得纯的或富集的平面手性二茂铁的对映体变得至关重要,这取决于有效的不对称合成程序和对映体分离方法的可用性。尽管如此,在对映体分离科学中,这些茂金属并没有得到全面的探索,迄今为止该领域的系统分析研究报道也很少。另一方面,有机和有机金属化学家经常使用对映选择性高效液相色谱法来测量通过不对称合成制备的平面手性二茂铁的对映体纯度。在这些基础上,本综述旨在通过讨论随着时间发展的液相对映分离方法,将这一主要主题与二茂铁化学最相关的方面相结合,为读者提供平面手性二茂铁对映分离的全面概述。因此,将简要总结二茂铁的主要结构特征和模拟此类茂金属的方法。此外,还将讨论具有应用兴趣的平面手性二茂铁以及制备某些类平面手性二茂铁的不对称合成的局限性,目的是将分析科学家引向“热门话题”和仍未解决的问题获得具有平面手性特征的二茂铁的对映异构体。
更新日期:2022-08-10
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