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平面手性:催化和结构发现的宝库。

Planar Chirality: A Mine for Catalysis and Structure Discovery.

机构信息

Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country (UPV/EHU), Manuel de Lardizabal 3, 20018, San Sebastián, Spain.

出版信息

Angew Chem Int Ed Engl. 2022 Mar 21;61(13):e202113504. doi: 10.1002/anie.202113504. Epub 2022 Jan 27.

DOI:10.1002/anie.202113504
PMID:34717037
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9304569/
Abstract

Planar chirality is one of the most fascinating expressions of chirality, which is exploited by nature to lock three-dimensional chiral conformations and, more recently, by chemists to create new chiral reagents, catalysts, and functional organic materials. Nevertheless, the shortage of procedures able to induce and secure asymmetry during the generation of these unique chiral entities has dissuaded chemists from exploiting their structural properties. This Minireview intends to illustrate the limited but remarkable catalytic methods that have been reported for the production of planar chirality in strained molecules and serve as a source of inspiration for the development of new unconventional procedures, which are expected to appear in the near future.

摘要

平面手性是手性最迷人的表现形式之一,自然界利用它来锁定三维手性构象,最近化学家也利用它来创造新的手性试剂、催化剂和功能有机材料。然而,在生成这些独特手性实体的过程中,能够诱导和稳定不对称的方法有限,这使得化学家们望而却步,无法充分利用它们的结构特性。这篇综述旨在介绍有限但引人注目的催化方法,这些方法已被报道用于产生应变分子中的平面手性,并为开发新的非常规方法提供灵感,预计这些方法将在不久的将来出现。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6ff/9304569/830c6c3bbfa2/ANIE-61-0-g017.jpg
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Chirality. 2021 Sep;33(9):506-527. doi: 10.1002/chir.23335. Epub 2021 Jul 24.
3
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Nat Commun. 2025 Apr 3;16(1):3170. doi: 10.1038/s41467-025-58241-3.
4
Pd/NHC sequentially catalyzed atroposelective synthesis of planar-chiral macrocycles.钯/氮杂环卡宾相继催化的平面手性大环化合物的对映选择性合成。
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