Ni-Catalyzed Reductive 1,2-Alkylarylation of Alkenes for the Synthesis of Spirocyclic γ-Lactams

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-06-24 DOI:10.1021/acs.orglett.4c01981
James W. Pearson, Teh Ren Hou, Jelena Golijanin, Patricia I. Stewart, Eun Seo Choi, Alexis L. Gabbey, Michael S. West and Sophie A. L. Rousseaux*, 
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Abstract

An intermolecular nickel-catalyzed reductive 1,2-alkylarylation of acrylates with cyclopropylamine NHP esters and aryl iodides is reported. This operationally simple protocol provides direct access to 1-alkylcyclopropylamine scaffolds. The mild conditions are compatible with four-membered α-amino strained rings as well as five- and six-membered ring systems. The products undergo cyclization to access α-arylated spirocyclic γ-lactams─a motif present in several pharmaceuticals.

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镍催化烯烃的 1,2-烷基芳香化反应以合成螺环 γ-内酰胺。
本研究报告介绍了分子间镍催化的丙烯酸酯与环丙胺 NHP 酯和芳基碘化物的还原性 1,2-烷基芳基化反应。这种操作简单的方案可直接获得 1-烷基环丙胺支架。温和的条件与四元α-氨基窄环以及五元和六元环系统兼容。这些产物经过环化反应后,可获得α-芳基化的螺环γ-内酰胺--一种存在于多种药物中的主题。
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来源期刊
Organic Letters
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.
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