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Synthesis of planar chiral ferrocenes via enantioselective remote C–H activation

发布时间：2026-06-21
点击次数：

影响因子：24.5
DOI码：10.1038/s41557-023-01176-3
发表刊物：Nature Chemistry
摘要：Planar chiral ferrocenes are widely studied structures in asymmetric catalysis, materials science and medicinal chemistry. Although synthetic methods for 1,2-disubstituted planar chiral ferrocenes are well known, methods for the direct construction of 1,3-disubstituted planar chiral ferrocenes remain elusive. Here we report a modular platform for the construction of planar chirality in 1,3-disubstituted ferrocenes/ruthenocenes via an enantioselective relay remote C–H activation strategy. This method demonstrates a mechanism for remote enantiocontrol via enantiodetermining initial C‒H activation at the C2 position, enabled by a chiral mono-N-protected natural amino-acid ligand, and subsequent relay to the remote C3 position by a bridgehead-substituted norbornene mediator. A wide variety of 1,3-disubstituted planar chiral metallocenes are prepared with high enantioselectivity (96‒99% e.e.). The reaction shows good functional-group tolerance and high step-economy, and aryl iodides/bromides are compatible as coupling partners. The resulting metallocenes can be readily derivatized to yield planar chiral ligands and catalysts for asymmetric catalysis as well as building blocks for other applications.
论文类型：期刊论文
学科门类：理学
卷号：6
期号：15
页面范围：815-823
ISSN号：1755-4349
是否译文：否
发表时间：2023-04-17
收录刊物：SCI
发布期刊链接：https://www.nature.com/articles/s41557-023-01176-3#citeas