Bifunctional NHC-Catalyzed Asymmetric Intramolecular Conjugate Addition via Noncovalent Interaction

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 DOI:10.1021/acs.orglett.5c00315

Ujjwal Maji, Arpita Baidya, Supriyo Das, Joyram Guin

引用次数: 0

Abstract

Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic and nucleophilic centers of substrates, the reaction proceeds through a well-organized transition state, thereby affording products with up to 94% ee and a broad scope. The process is found to be scalable. The initial mechanistic study supports the bifunctional nature of the newly designed NHC.

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在此，我们报告了一种含有手性双官能团 N-杂环碳烯（NHC）的新型方酰胺及其在开发涉及非共价相互作用的不对称分子内共轭加成反应中的应用。通过同时激活底物的亲电中心和亲核中心，反应通过一个组织良好的过渡态进行，从而得到ee高达94%的产物，且范围广泛。该过程具有可扩展性。初步的机理研究支持了新设计的 NHC 的双功能性质。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.