Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes†

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-03-25 DOI:10.1039/D4SC08753D

Anirban Maity, Kuruva Balanna, Constantin G. Daniliuc and Armido Studer

引用次数: 0

Abstract

Cyclobutanes are strained carbocycles found in many drugs and natural products. Herein, we report a diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes with tert-butylnitrite and TEMPO to access 1,1,3-trisubstituted cyclobutanes. Various bicyclo[1.1.0]butanes effectively participated in the radical reaction yielding the substituted cyclobutane scaffolds with excellent yields and diastereoselectivity. The reaction is catalyst-free, easy to perform, and scalable and can be conducted in open air. Products obtained serve as substrates for the synthesis of 1,1,3,3-tetrasubstituted cyclobutanes with good yields and diastereoselectivity.

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双环[1.1.0]丁烷的非对映选择性1,3-硝基氧化。

环丁烷是在许多药物和天然产物中发现的一种张力碳环。在这里，我们报道了一种非对映选择性的1,3-硝基氧化双环[1.1.0]丁烷与叔丁基亚硝酸盐和TEMPO得到1,1,3-三取代环丁烷。多种双环[1.1.0]丁烷有效参与自由基反应，生成了产率和非对映选择性优异的取代环丁烷支架。该反应无催化剂，易于进行，可扩展，可在露天进行。所得产物可作为底物，合成收率高、非对映选择性好的1,1,3,3-四取代环丁烷。

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

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.