联吡啶-N,N′-二氧化物催化剂：设计、合成及在 1H-吡唑并[3,4-b]吡啶类似物不对称合成中的应用

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-04-18 DOI:10.1021/acs.orglett.4c00515

Shijie Zhu, Xue Tian, Jichang Liu*, Bin Dai* and Shi-Wu Li*,

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引用次数: 0

摘要

研究人员开发了一种新型高效手性 C2 对称双吡啶-N,N′-二氧配体，用于催化 5-氨基吡唑与 α,β-不饱和 2-酰基咪唑的迈克尔加成/环化反应，在催化剂负载较低的温和条件下，以 85-97% 的产率和高达 99% 的对映体选择性获得相应的加合物。值得注意的是，该方案在反应性和对映体选择性方面具有优势，低至 2.2 摩尔%的 L1 和 2.0 摩尔%的 Ni(OTf)2 就能促进克级规模的标题反应，以优异的对映体选择性得到所需的产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

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Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

A novel type of highly efficient chiral C2-symmetric bipyridine-N,N′-dioxides ligand application in catalyzing Michael addition/Cyclization of 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts in 85–97% yield with up to 99% enantioselectivity under mild conditions with a lower catalyst loading and broad scope. Remarkably, this protocol exhibits advantages in terms of reactivity and enantioselectivity, giving the fact that as low as 2.2 mol % of L1 and 2.0 mol % of Ni(OTf)₂ can promote the title reaction on gram scale to afford the desired product with excellent enantioselectivity.

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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.