n -杂环碳催化的化学和对映选择性三组分酯化/酰胺化反应获得平面手性二茂铁衍生物

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-04-01 DOI:10.1021/acscatal.4c07576

Youlin Deng, Xinghua Wang, Haitao Liu, Hui Cai, Chaoyang Song, Yonggui Robin Chi, Donghui Wei, Zhichao Jin

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引用次数: 0

摘要

揭示了一种n -杂环碳（NHC）催化的三组分酯化/酰胺化接力策略，以方便地获得富含对映体的平面手性二茂铁衍生物。催化接力中的酯化和酰胺化反应以化学选择性和对映选择性的方式依次进行。通过实验和计算两种方法揭示了反应机理，并指出氢键相互作用和催化体系中的碱性添加剂对反应的化学选择性和立体选择性起着至关重要的作用。平面手性二茂铁酯酰胺产品在合成多种新型不对称催化配体和开发作物保护手性杀菌剂方面具有重要的应用前景。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

N-Heterocyclic Carbene-Catalyzed Chemo- and Enantioselective Three-Component Esterification/Amidation Relay for Access to Planar Chiral Ferrocene Derivatives

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N-Heterocyclic Carbene-Catalyzed Chemo- and Enantioselective Three-Component Esterification/Amidation Relay for Access to Planar Chiral Ferrocene Derivatives

An N-heterocyclic carbene (NHC)-catalyzed three-component esterification/amidation relay strategy was disclosed for facile access to enantio-enriched planar chiral ferrocene derivatives. The esterification and amidation reactions in the catalytic relay proceeded in sequence in both chemoselective and enantioselective fashions. Both experimental and computational methods were used to reveal the reaction mechanism and indicated that both the hydrogen-bonding (H-bonding) interactions and the basic additives in the catalytic system had played crucial roles in the reaction chemo- and stereoselectivities. The planar chiral ferrocene-based ester–amide products showed interesting applications in the synthesis of multiple novel ligands for asymmetric catalysis and the development of chiral bactericides for crop protection.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.