Staudinger Ketene-Imine Cycloaddition, RCM Approach to Macrocrocyclic Bisazetidinones

摘要

Application of Staudinger ketene-imine cycloaddition reaction to bis-o-allyloxyarylideneamines afforded the corresponding bisallyloxyazetidinones as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs’ catalysts afforded the corresponding macrocyclic bisazetidinones in good yields. The cis-anti-cis bisazetidinones are readily identified by 1H NMR using Eu(hfc)3 chiral shift reagent.