Synthesis of (Diethoxyphosphoryl)acetonitrile Oxide and Its Cycloaddition to Olefins. Synthetic Applications to 3,5-Disubstituted 2-Isoxazolines
- 1 July 1987
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (7) , 2463-2473
- https://doi.org/10.1246/bcsj.60.2463
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.Keywords
This publication has 21 references indexed in Scilit:
- The isoxazoline route to the molecules of natureAccounts of Chemical Research, 1984
- Reduction of .DELTA.2-isoxazolines. 3. Raney nickel catalyzed formation of .beta.-hydroxy ketonesJournal of the American Chemical Society, 1983
- Methods for the stereoselective cis-cyanohydroxylation and -carboxyhydroxylation of olefinsThe Journal of Organic Chemistry, 1983
- Methods for the conversion of isoxazolines to β-hydroxy ketonesTetrahedron Letters, 1982
- Benzenesulfonylnitrile oxide: a useful intermediate for the syn-cyanohydroxylation of alkenesJournal of the American Chemical Society, 1979
- Photoelectron spectra of 3-substituted cyclopentenes. Correlations between ionization potentials and cycloaddition regioselectivityJournal of the American Chemical Society, 1978
- Eliminierende Ringöffnung von 2‐Isoxazolinen: ein neuer Weg zu α,β‐ungesättigten KetonenAngewandte Chemie, 1976
- Interchange of functionality in conjugated carbonyl compounds through isoxazolesJournal of the American Chemical Society, 1972
- Synthesis of corrins and related ligands. I. General approach and model studiesJournal of the American Chemical Society, 1971
- The Chemistry of the 2-Isoxazolines: Reductive CleavagesJournal of the American Chemical Society, 1957