Staudinger synthesis

For the reaction that reduces azides to amines using phosphorus compounds, see Staudinger reaction.

The Staudinger synthesis, also called the Staudinger ketene-imine cycloaddition, is a chemical synthesis in which an imine 1 reacts with a ketene 2 through a non-photochemical 2+2 cycloaddition to produce a β-lactam 3.[1] The reaction carries particular importance in the synthesis of β-lactam antibiotics.[2] The Staudinger synthesis should not be confused with the Staudinger reaction, a phosphine or phosphite reaction used to reduce azides to amines.

Reviews on the mechanism, stereochemistry, and applications of the reaction have been published.[3][4][5]

  1. ^ Li, Jie Jack, ed. (2010). Name reactions for carbocyclic ring formations. Hoboken, N.J.: Wiley. p. 45. ISBN 9780470872208.
  2. ^ Tidwell, T. 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.
  3. ^ Fu, N.; Tidwell, T. T. "Preparation of β-lactams by [2+2] cycloaddition of ketenes and imines" Tetrahedron 2008, 64, 10465-10496. ([1])
  4. ^ Georg, Gunda I. (1992). Organic Chemistry of β-Lactams. New York: Verlag Chemie. ISBN 978-0471187998.
  5. ^ Cossio, F. P.; Arrieta, A.; Sierra, M. G. (2008). "The Mechanism of the Ketene-Imine (Staudinger) Reaction in Its Centennial: Still an Unsolved Problem?". Accounts of Chemical Research. 41 (8): 925–936. doi:10.1021/ar800033j. PMID 18662024.