Sequential Staudinger Ketene− Imine Cycloaddition, RCM Approach to Highly Rigid Macrocrocyclic Bisazetidinones

…, TF Al-Azemi, MD Abd El-Halim

Index: Ibrahim, Yehia A.; Al-Azemi, Talal F.; Abd El-Halim, Mohamed D. Journal of Organic Chemistry, 2010 , vol. 75, # 13 p. 4508 - 4513

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Citation Number: 9

Abstract

An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene− imine cycloaddition of o- allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene− imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of ...