Kinugasa reaction
The Kinugasa reaction is a chemical reaction that is used to produce β-lactams. It is named after its discoverer Manabu Kinugasa . In a Kinugasa reaction, nitrones are reacted with terminal alkynes in the presence of catalytic or stoichiometric amounts of copper (I) salts to form β-lactams.
mechanism
The copper forms an acetylide with the alkyne. Then a 1,3-dipolar cycloaddition takes place between the nitrone and the acetylide. The organyl copper thus formed rearranges via a ketene intermediate and the β-lactam is formed.
Individual evidence
- ↑ Manabu Kinugasa, Shizunobu Hashimoto: J. Chem. Soc. Chem. Commun. 1972 , 466-467.
- ↑ José Marco-Contelles: "β-Lactam Synthesis by the Kinugasa Reaction", in 2004 , 43 , 2198-2200, doi : 10.1002 / anie.200301730 .