What is it about?
This study describes a new method for synthesizing 3-azabicyclo[3.1.0]hexanes, an important class of bicyclic nitrogen-containing compounds found in biologically active molecules. The key step is the generation of magnesium cyclopropylidenoids from sulfoxide precursors, followed by an intramolecular insertion into a carbon–hydrogen bond adjacent to nitrogen. The reaction proceeds efficiently for a variety of substrates and can also be applied to the synthesis of optically active products.
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Why is it important?
3-Azabicyclo[3.1.0]hexanes are valuable structural motifs in medicinal chemistry because they appear in natural products and pharmaceutical compounds. Conventional syntheses often require multiple steps or pre-functionalized substrates. This work provides an efficient alternative by directly constructing the bicyclic framework through C–H bond functionalization, offering a practical approach to these useful molecules.
Perspectives
We found that magnesium cyclopropylidenoids generated from 1-chlorocyclopropyl p-tolyl sulfoxides can insert into an unactivated C–H bond adjacent to nitrogen to efficiently form 3-azabicyclo[3.1.0]hexanes. We hope to further explore the unique reactivity of magnesium cyclopropylidenoids and develop new synthetic methods based on their C–H insertion chemistry.
Associate Professor Tsutomu Kimura
Read the Original
This page is a summary of: Synthesis of 3-azabicyclo[3.1.0]hexanes by insertion of cyclopropylmagnesium carbenoids into an intramolecular C–H bond adjacent to a nitrogen atom, Tetrahedron, September 2015, Elsevier,
DOI: 10.1016/j.tet.2015.02.059.
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