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Tandem processes for the synthesis of carbocycles

21 April 2020
Tandem processes for the synthesis of carbocycles

Michal Šimek and Ullrich Jahn show in their Angewandte Chemie paper how to rapidly construct functionalized carbocycles in atom economic steps enabled by a clever merger of pericyclic and radical reactions.

The authors present in their communication a reaction sequence that begins with a [3,3]-rearrangement, which modifies the carbon skeleton, puts a double bond where it needs to be for cyclization and installs an alkoxyamine handle at the same time. This unit is then relocated onto the double bond in a rare 5-endo-trig cyclization step, forming cyclopentanes with the alkoxyamine as a useful oxygen functionality for further transformations.

The overall process broadens the repertoire of tools for chemists in the synthesis of complex molecules and will serve as a blueprint for further development and applications for chemistry and biology. 

Original paper: Šimek, M., Bártová, K., Pohl, R., Císařová, I., & Jahn, U. (2020). Tandem Anionic oxy-Cope Rearrangement/Oxygenation Reactions as a Versatile Method for Approaching Diverse Scaffolds. Angewandte Chemie International Edition. doi:0.1002/anie.201916188 
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