Controlled Generation of Unstabilized N -Alkyl Nitrile Imines Enables Regioselective (3 + 2) Cycloadditions with Diverse Dipolarophiles

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2026-10-14 DOI:10.1021/acs.orglett.6c03912

Matthew C. Lamb,Tristan H. Lambert

引用次数: 0

Abstract

Abstract N-Alkyl nitrile imines remain underdeveloped as intermediates for intermolecular cycloadditions. Here, we report their in situ generation and regioselective (3 + 2) cycloaddition with activated and unactivated alkenes and alkynes, affording N-alkyl pyrazolines and pyrazoles in good to excellent yields. The method accommodates broad variation in both reaction partners and enables gram-scale preparation of a key pyrazole fragment used in the synthesis of lenacapavir in a 79% yield over two steps.

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控制生成不稳定的N -烷基腈亚胺使区域选择性（3 + 2）环加成物具有不同的亲偶极试剂

摘要n -烷基腈亚胺作为分子间环加成的中间体尚不发达。在这里，我们报道了它们的原位生成和区域选择性（3 + 2）环加成与活化和未活化的烯烃和炔，提供了n -烷基吡唑啉和吡唑在良好到优异的产量。该方法适应两种反应伙伴的广泛变化，并且能够在两步内以79%的收率制备用于合成lenacapavir的关键吡唑片段的克级制备。

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.