Synthesis and 1,3-dipolar cycloaddition reactions of 4-methyl-1-nitromethyl-2,6,7-trioxabicyclo[2.2.2]octane

The preparation of novel 3-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl)-Delta(2)-isoxazolines 2 via nitrile oxide cycloaddition chemistry is described. The target compounds were produced in moderate to good yields using only 2.2 equivalents of alkene and without the need for slow addition of reagents. Cycloaddition reactions were conducted using modified Mukaiyama conditions that included a convenient dehydration reagent which significantly simplified product isolation. (C) 1999 Elsevier Science Ltd. All rights reserved.