Maity Anirban, Balanna Kuruva, Daniliuc Constantin G, Studer Armido
Organisch-Chemisches Institut, Universität Münster Corrensstraße 40 48149 Münster Germany
Chem Sci. 2025 Mar 25;16(17):7264-7269. doi: 10.1039/d4sc08753d. eCollection 2025 Apr 30.
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 -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.
环丁烷是存在于许多药物和天然产物中的张力碳环。在此，我们报道了用亚硝酸叔丁酯和TEMPO对双环[1.1.0]丁烷进行非对映选择性1,3-硝基氧化反应，以得到1,1,3-三取代环丁烷。各种双环[1.1.0]丁烷有效地参与了自由基反应，以优异的产率和非对映选择性得到了取代环丁烷骨架。该反应无催化剂，易于操作且可放大规模，并且可以在空气中进行。所得到的产物可作为合成1,1,3,3-四取代环丁烷的底物，产率和非对映选择性良好。
