Eschenmoser Coupling

• 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. 1967, 6, 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

• Examples

• Experimental Procedure

• Experimental Tips

• References

• Related Reactions

• Barton-Kellogg Reaction 
• Lawesson’s Reagent

• Related Books

• External Links

synthesis of enamines