ChemInform Abstract: 1,3‐Dipolar Cycloaddition of Acetonitrile Oxide to Δ²³‐20‐Hydroxysteroids.

Abstract

1,3-Dipolar Cycloaddition of Acetonitrile Oxide to ∆ 23 -20-Hydroxysteroids.-Cycloaddition of acetonitrile oxide, generated in situ from aldoxime (IV), to the title steroidic alkenes (III) and (VII) affords a 1:1 mixture of diastereomeric isoxazolines (V) and (VIII), resp., demonstrating that the β-hydroxy group (in contrast to the previously studied steroidic α-hydroxyalkenes) has no influence on the stereochemical outcome of the reaction. -(LITVINOVSKAYA, R. P.; DRACH, S. V.; ERMOLENKO, E. A.; KHRIPACH, V. A.; Zh.