What is it about?
This study describes a new method for making 2-azabicyclo[2.1.0]pentanes, a class of compact nitrogen-containing molecules that are difficult to prepare but are valuable in medicinal chemistry. We designed special cyclopropane intermediates that contain both a reactive carbon center and a nitrogen nucleophile in the same molecule. These intermediates undergo an intramolecular ring-closing reaction to efficiently form the bicyclic framework. The method works for a variety of substrates and can also produce optically active products with high enantiomeric purity.
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Why is it important?
Rigid nitrogen-containing ring systems are useful building blocks in pharmaceutical research because their fixed three-dimensional shapes can improve the biological properties of drug candidates. However, these molecules have been difficult to synthesize efficiently. Our method provides a practical and versatile approach to preparing these challenging structures. It also demonstrates how highly reactive cyclopropylmagnesium carbenoids can be used to construct strained bicyclic molecules through intramolecular carbon–nitrogen bond formation, expanding the synthetic toolbox available to organic chemists.
Perspectives
The unique reactivity of cyclopropylmagnesium carbenoids may also enable the development of new carbon–heteroatom bond-forming reactions and provide access to structurally diverse molecular scaffolds for medicinal chemistry and chemical biology.
Associate Professor Tsutomu Kimura
Read the Original
This page is a summary of: Synthesis of 2-azabicyclo[2.1.0]pentanes by the intramolecular nucleophilic substitution of cyclopropylmagnesium carbenoids with magnesium anilide, Tetrahedron, May 2017, Elsevier,
DOI: 10.1016/j.tet.2017.03.045.
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