Abstract
Spirocyclobutanes have gained significant attention in medicinal chemistry discovery
programs due to their broad spectrum of biological activities and clinical applications.
Utilizing ring strain in small molecules to drive organic transformations is one of
the most powerful tools in chemical synthesis. Our research group has focused on developing
new synthetic strategies enabled by ring strain to construct complex molecules selectively
and efficiently. This account summarizes our recent efforts toward the synthesis of
a library of functionalized spirocyclobutanes by harnessing the ring strain of bicyclo[1.1.0]butanes.
Three spicrocyclization cascades have been developed to incorporate a diverse range
of radical precursors into spirocycobutanes.
1 Introduction
2 Synthesis of Spirocyclobutyl Lactones and -Lactams using Bifunctional Reagents
3 Dual Photoredox/Nickel Catalysis for the Synthesis of Spirocyclobutyl Lactams
4 Synthesis of Spirocyclobutyl Oxindoles under Photoredox Catalysis
5 DFT Studies
6 Conclusion
Key words
bicyclo[1.1.0]butane - strain-release - photoredox catalysis - radicals - spirocyclobutanes
- dual catalysis - bifunctional reagents
