卤素-邦德辅助 NHC 催化（动态）动力学解析用于杂环丁烷的无选择性合成

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-15 DOI:10.1021/acs.orglett.4c03346

Shao-Jie Wang, Li-Rong Jiang, He Wang, Tian-Yi Hu, Ling Zhou, Jie Chen

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引用次数: 0

摘要

我们报告了一种新型卤素键辅助 NHC 催化（动态）动力学解析策略，用于合成轴向手性杂环丁烷。使用 3-5 mol % 的 NHC 催化剂，可以高效地制备出一类对映体选择性极佳（≤98% ee）的轴向手性喹啉类化合物。机理研究揭示了 5-溴-2-碘苯甲醛在该反应中的不可或缺性，其中关键的卤素键相互作用在该过程中起着至关重要的作用。

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Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic Resolution for the Atroposelective Synthesis of Heterobiaryls

We report a novel halogen-bond-assisted NHC-catalyzed (dynamic) kinetic resolution strategy for the synthesis of axially chiral heterobiaryls. A class of axially chiral quinolines are prepared efficiently in excellent enantioselectivities (≤98% ee) employing 3–5 mol % NHC catalyst. Mechanistic studies reveal the indispensability of 5-bromo-2-iodobenzaldehyde in this reaction, in which a pivotal halogen bonding interaction plays a crucial role in the process.

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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.