Nitrile oxide cycloaddition reactions of alkenes or alkynes and nitroalkanes substituted with O-alkyloxime groups convertible to various functional groups
01 natural sciences
0104 chemical sciences
DOI:
10.1016/j.tetlet.2020.152213
Publication Date:
2020-07-06T15:10:18Z
AUTHORS (3)
ABSTRACT
Abstract Nitrile oxides, which are easily generated in situ from widely available nitroalkanes, can be used to directly access 2-isoxazoline heterocycles through 1,3-dipolar cycloaddition reactions with alkenes. These heterocycles are not only useful core fragments in pharmaceutical and agricultural chemistry, but also valuable building blocks convertible to multifunctional groups, such as β-hydroxy ketones. Herein, we have developed nitrile oxide cycloaddition reactions between nitrile oxides derived from O-alkyloxime-substituted nitroalkanes and various alkenes. This methodology can be applied to construct 2-isoxazolines possessing electron-withdrawing groups, which are difficult to access using the conventional approach.
SUPPLEMENTAL MATERIAL
Coming soon ....
REFERENCES (22)
CITATIONS (11)
EXTERNAL LINKS
PlumX Metrics
RECOMMENDATIONS
FAIR ASSESSMENT
Coming soon ....
JUPYTER LAB
Coming soon ....