通过非共价活化催化 N-杂环羰基不对称 SN2 烷基化反应。

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-09-13 Epub Date: 2024-08-02 DOI:10.1021/acs.orglett.4c02082

En Li, Xiaoyun Liao, Fangfang Guo, Yong Huang, Jiean Chen

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引用次数: 0

摘要

通过探索非共价相互作用，特别是 N-杂环碳烯介导的过程，不对称催化领域得到了发展。尽管兼容的亲电体（主要是 π 受体）数量有限，但本研究首次提出了使用 Csp3 亲电体对 3- 芳基吲哚进行不对称 α 烷基化反应。该创新方案将多种羰基吲哚与烷基、烯丙基和丙炔基亲电体结合在一起，实现了高产率和高对映选择性。初步的机理探索支持一种非共价催化机制，增强了构建具有潜在应用价值的复杂手性分子的工具包。

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 Asymmetric SN2 Alkylation via Noncovalent Activation.

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N-Heterocyclic Carbene-Catalyzed Asymmetric S_N2 Alkylation via Noncovalent Activation.

The field of asymmetric catalysis has been developed by exploring noncovalent interactions, particularly within N-heterocyclic carbene-mediated processes. Despite challenges due to the limited number of compatible electrophiles (predominantly π-acceptors), this study introduces the first asymmetric α-alkylation of 3-aryl oxindoles using C_sp3 electrophiles. The innovative protocol integrates diverse oxindoles and alkyl, allyl, and propargyl electrophiles, achieving high yields and enantioselectivities. Preliminary mechanistic explorations support a noncovalent catalytic mechanism, enhancing the tool kit for constructing complex chiral molecules with potential applications.

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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.