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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Staudinger ketene-imine cycloaddition, RCM approach to macrocrocyclic bisazetidinones
Yehia A Ibrahim1, Talal F Al-Azemi, Mohamed D Abd El-Halim
1Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. yehiaai@kuc01.kuniv.edu.kw
Abstract:
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 (1)H NMR using Eu(hfc)(3) chiral shift reagent.
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