O. Tsuge, S. Kanemasa, H. Suga
Jul 1, 1987
Citations
0
Influential Citations
31
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
(Diethoxyphosphoryl)acetonitrile oxide undergoes regioselective cycloaddition to olefins leading to 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines or -isoxazole. The phosphorus-stabilized carbanions generated by deprotonation of the cycloadducts can be utilized for the condensation with carbonyl compounds, alkylation, and oxidation with oxygen to provide 3,5-disubstituted 2-isoxazolines as useful synthetic building blocks. Raney nickel hydrogenolysis of 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines gives β-hydroxy-β′-phosphoryl ketones bearing a variety of functional groups, which can be further converted into α,β-unsaturated β′-phosphoryl ketones.