Teaching Proline New Tricks

Teaching Proline New Tricks

Author: ChemistryViews.org

α-Ketols can be dehydrogenated to give ketones (pictured). Usually, metal-based reducing agents are used for this type of reaction (e.g., Zn, Li, or Sm reagents). Known approaches generally require dry conditions, multiple steps, and/or the protection of hydroxyl groups. They also do not provide good functional group tolerance.

Dmitry Tsvelikhovsky and colleagues, The Hebrew University of Jerusalem, Israel, have developed a metal-free, easy-to-operate, proline-promoted dehydroxylation of α-ketols. The team used proline as a reducing agent, potassium acetate as a base, and dimethylsulfoxide (DMSO) as the solvent. The reaction was performed at 100–130 °C and gives the desired ketones in generally good yields.

The reaction can be performed in an open flask and tolerates other functional groups. The method demonstrates a previously unknown reactivity of proline.


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