KF/Al₂O₃: Solid-Supported Reagent Used in 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide

Abstract

The stereoselective synthesis of 2-isoxazolidine through 1,3-dipolar cycloaddition reaction of nitrile oxide, which is in situ generation from aldoxime in the presence of N-bromosuccinamide and solid-supported reagent KF/Al₂O₃ at room temperature, is reported. KF/Al₂O₃ is sufficiently basic such that it can replace organic bases such as Et₃N used in typical procedures and it catalyses the reaction to enhance the rate of the reaction.

GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dipolar cycloaddition reaction
• KF/Al₂O₃
• NBS
• nitrile oxide
• solid-supported reagent

ACKNOWLEDGMENTS

We gratefully acknowledge the Department of Science and Technology, New Delhi, for the financial support to carry out the work. Also the author thanks the director, North East Institute of Science and Technology, Jorhat, Assam, and Indian Institute of Technology, Delhi.

Notes

^a Products have been identified from their respective spectral (IR,¹H NMR,¹³C NMR, mass, GC), physical data and comparison with authentic samples.

^b Yields mentioned are the isolated yield, determined by GC and based on reactant.