Diastereoselective Propionitrile Oxide Cycloaddition Reactions With Some γ-Substituted α-Methylene-γ-butyrolactones

Abstract

A number of γ-substituted α-methylene-γ-butyrolactone derivatives underwent 1,3-dipolar cycloaddition with propionitrile oxide to give spiro Δ²-isoxazolines. The reaction proceeded regiospecifically and with high diastereoselectivity. The products of anti addition predominated. The regiochemistry of addition and relative stereochemistry of the products were determined by a combination of n.O.e ., HETCOR and DOUBTFUL n.m.r. experiments. The assignment was confirmed in one case by X-ray crystallography.