手性双芳基 N-杂环羰基钯催化剂，具有用于对映选择性不对称 C-N 交叉偶联的 C-H-Pd 交互作用

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-11 DOI:10.1021/acs.orglett.4c03709

Woosong Han, Huijeong Ryu, Changmuk Kang, Sukwon Hong

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引用次数: 0

摘要

新型手性双芳基咪唑并[1,5-a]吡啶碳钯配合物（ImPy-Pd）具有C-H-Pd相互作用和C5-芳基取代基，该配合物已被开发并成功应用于Pd催化的丙二酰胺衍生物的对映选择性非对称C-N交叉偶联反应、高产率（≤99%）和对映选择性（≤97：3 er）。手性催化剂通过与立体笨重的取代基发生负相互作用，限制取代基围绕金属中心旋转，从而实现立体控制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Chiral Biaryl N-Heterocyclic Carbene–Palladium Catalysts with Anagostic C–H···Pd Interaction for Enantioselective Desymmetric C–N Cross-Coupling

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Chiral Biaryl N-Heterocyclic Carbene–Palladium Catalysts with Anagostic C–H···Pd Interaction for Enantioselective Desymmetric C–N Cross-Coupling

Novel chiral biaryl imidazo[1,5-a]pyridine carbene–palladium complexes (ImPy–Pd) featuring an anagostic C–H···Pd interaction and a C5-aryl substituent have been developed and successfully applied to the Pd-catalyzed enantioselective desymmetric C–N cross-coupling of malonamide derivatives, providing chiral 3,4-dihydroquinoline-2-ones with quaternary stereocenters in high yields (≤99%) and enantioselectivities (≤97:3 er). The chiral catalyst exerts stereocontrol by restricting the rotation of substituents around the metal center through anagostic interactions with sterically bulky substituents.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.