硒催化的二烯烃和二烯酸酯衍生物的区域选择性分子间二胺化反应

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-09-30 DOI:10.1021/acs.orglett.4c03431

Alexander F. Dohoda, Victoria L. Zottarelli, Dureti Hajikedir, Forrest E. Michael

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引用次数: 0

摘要

我们报告了一种利用氨基磺酸盐作为方便氮源的硒催化二烯烃二胺化反应。该反应在取代程度较低的烯烃上进行 1,2-加成时具有区域选择性，而无需使用系链二胺。我们还首次报告了二烯丙基磷酸酯和对甲苯磺酸盐的二胺化反应，从而以高同步非对映选择性得到了合成上有用的 α,β-二氨基酮衍生物。密度泛函理论计算支持通过二烯与硒双亚胺的[4+2]环加成，然后进行开环氨解和[2,3]-三向异性重排的机理。

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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Selenium-Catalyzed Regioselective Intermolecular Diamination of Dienes and Dienolate Derivatives

We report a selenium-catalyzed diamination of dienes using sulfamates as a convenient nitrogen source. This reaction proceeds regioselectively for 1,2-addition at the less substituted alkene, without the need for a tethered diamine. We also report the first diamination of dienyl phosphates and tosylates, affording synthetically useful α,β-diaminoketone derivatives with high syn diastereoselectivity. Density functional theory calculations support a mechanism proceeding via [4+2] cycloaddition of the diene with a selenium bis(imide), followed by ring-opening aminolysis and [2,3]-sigmatropic rearrangement.

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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.