Eschenmoser Coupling

Eschenmoser Coupling

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  • General Characteristics

The Eschenmoser coupling begins with the S-alkylation of thioamides and gives enamine products (vinylogous amides, urethanes, etc.). As shown below, thiophiles (e.g. triphenylphosphine) are used to eliminate the sulfur.

  • General References

  • Fischli, A.; Eschenmoser, A. Angew. Chem. Int. Ed. 19676, 866. DOI: 10.1002/anie.196708661
  • Roth, M.; Dubs, P.; Gotschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710. DOI: 10.1002/hlca.19710540229
  • Shiosaki, K. Comp. Org. Syn. 1991, 2, 865.
  • Reaction Mechanism


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