Diastereoselective 1,3-nitrooxygenation of bicyclo[1.1.0]butanes
Anirban Maity1, Kuruva Balanna1, Constantin G Daniliuc1
1Organisch-Chemisches Institut, Universität Münster Corrensstraße 40 48149 Münster Germany studer@uni-muenster.de.
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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