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. 2014 Aug 15;79(16):7607-15.
doi: 10.1021/jo501339c. Epub 2014 Jul 31.

Hetero-Diels-Alder reaction of phosphorylated nitroso alkenes with enol ethers on water: a clean approach toward 1,2-oxazine derivatives

Jesús M de Los Santos  1 , Roberto Ignacio, Zouhair Es Sbai, Domitila Aparicio, Francisco Palacios
Affiliations

Hetero-Diels-Alder reaction of phosphorylated nitroso alkenes with enol ethers on water: a clean approach toward 1,2-oxazine derivatives

Jesús M de Los Santos et al. J Org Chem. .

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.

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