Remarkable Stereocontrol in 1,3-Dipolar Cycloaddition of Acyclic Nitrones: Investigation of the Cycloaddition of C,N-Diaryl Nitrones to Methyl Cinnamate Under Different Reaction Conditions

Abstract

Investigation of the cycloaddition of C,N-diarylnitrones to methyl cinnamate under different reaction conditions were carried out. Two diastereoisomeric and one regioisomeric cycloadducts were isolated and characterized by spectroscopic and x-ray data. Remarkable change in selectivity was noticed in solvent-free condition and in the presence of ytterbium triflate as catalyst.

Keywords:

• Cycloaddition
• isoxazolidine
• methyl cinnamate
• nitrone
• ytterbium triflate

ACKNOWLEDGMENT

The authors thank the Indian Council for Cultural Relations (ICCR) for financial assistance to P. K. Biswas (present address: BCSIR Laboratory, Dhanmondi, Dhaka-1205, Bangladesh).

Notes

Present affiliation for Debasish Bandyopadhyay: Department of Chemistry, University of Texas–Pan American, Edinburg, Texas, USA.