Serini reaction

What is Serini reaction?

The Serini reaction, which involves a zinc-promoted rearrangement of 17-hydroxy-20-acetoxy-steroids into 20-oxo-steroid derivatives with complete stereochemical inversion at C-17, was initially reported by Serini in 1939. This reaction is also commonly referred to as the Logemann-Serini reaction or Serini-Logemann reaction.

Serini reaction - general reaction scheme - Logemann-Serini reaction - Serini-Logemann reaction
Serini reaction

R = side chain (see list of acronyms)

The role of zinc in this reaction is to generate a Lewis acid, as demonstrated by the fact that treatment of steroid derivatives with anhydrous zinc acetate results in similar outcomes to refluxing with zinc. This reaction has been extended to other cyclic and open-chain 1,2-diol monoacetates, as well as the corresponding benzoates and p-nitrobenzoates.

The 1,2-diol monobenzoates or p-nitrobenzoates typically yield better results than the corresponding monoacetates under normal conditions. If the secondary carbon is attached to an aromatic ring, the reaction may produce the corresponding aldehyde due to 1,2-aryl migration.

References

Serini, A., Logemann, W. and Hildebrand, W., Ber., 1939, 72, 391

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