Staudinger synthesis

The Staudinger synthesis[1], named after the German chemist Hermann Staudinger, is a method to prepare β-lactams. An imine reacts with a ketene in a formal [2+2]-cycloaddition to give the cyclic amide.

History

The reaction was discovered in 1907[2] but did not attract much interest until the 1940s, when the structure of penicillin was elucidated. The β-lactam moiety of the first synthetic penicillin was constructed using this cycloaddition,[3] and it remains a valuable tool in synthetic organic chemistry.

References

  1. ^ Tidwell, Thomas T. (2008). "Hugo (Ugo) Schiff, Schiff Bases, and a Century of β-Lactam Synthesis". Angew. Chem. Int. Ed. 47 (6): 1016–1020. doi:10.1002/anie.200702965. PMID 18022986. 
  2. ^ H. Staudinger (1907). "Zur Kenntniss der Ketene. Diphenylketen". Justus Liebigs Ann. Chem. 356: 51–123. doi:10.1002/jlac.19073560106. 
  3. ^ J.C. Sheehan, E.L. Buhle, E.J. Corey, G.D. Laubach, J.J. Ryan (1950). J. Am. Chem. Soc. 72 (8): 3828–9. doi:10.1021/ja01164a534.