Synthesis of 2-(1-Phosphoryalkyl)- and 2-(1-Alkenyl)furans through Nitrile Oxide Cycloaddition Route

Article abstract of DOI:10.1246/bcsj.61.2133

A new synthetic method of 2-(1-phosphoryalkyl)furans with a variety of substituents on the ring is presented.Cycloaddition of (diethoxyphosphoryl)acetonitrile oxide to O-protected allyl alcohols is followed by a simple sequential procedure including Raney Ni reduction and acid treatment to give 2-(1-phosphorylmethyl)furans.The phosphorus-stabilized carbanions derived from the phosphorus-functionalized furans are applied to alkylation, oxidation with oxygen, or olefination to provide 2-(1-phosphorylalkyl)furans, 2-acylfurans, or 2-(1-alkenyl)furans, respectively.Some other synthetic applications are also described.