Hetero-Diels-Alder Reaction of Phosphorylated Nitroso Alkenes with Enol Ethers on Water: A Clean Approach Toward 1,2-Oxazine Derivatives
- Egileak:
- Jesús M. de los Santos, Roberto Ignacio, Zouhair Es Sbai, Domitila Aparicio, Francisco Palacios
- Urtea:
- 2014
- Aldizkaria:
- The Journal of Organic Chemistry
- Liburukia:
- 79
- Hasierako orria - Amaierako orria:
- 7607 - 7615
- Deskribapena:
-
A concise and eco-friendly synthesis of highly functionalized 1,2-oxazines from phosphinyl- and phosphonyl-nitroso alkenes has been developed. The key step of this process, which involves a two-step sequence of reactions on-water, is a regioselective hetero-Diels–Alder cycloaddition reaction of enol ethers to 4-phosphinyl or 4-phosphonyl nitroso alkenes mediated by water itself. The process has also been performed under solvent-free conditions and in organic solvents for comparison.