title: Hetero-Diels-Alder reaction of phosphorylated nitroso alkenes with enol ethers on water: a clean approach toward 1,2-oxazine derivatives.
abstract: 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.
authors: Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados "Lucio Lascaray", Universidad del País Vasco , Paseo de la Universidad 7, 01006 Vitoria, Spain.
authors: Jesús M
authors: JM
authors: de Los Santos
authors: Roberto
authors: R
authors: Ignacio
authors: Zouhair
authors: Z
authors: Es Sbai
authors: Domitila
authors: D
authors: Aparicio
authors: Francisco
authors: F
authors: Palacios
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000475:Alkenes; D004987:Ethers; D009603:Nitroso Compounds; D010078:Oxazines; D012997:Solvents; D014867:Water