Staudinger ketene-imine cycloaddition, RCM approach to macrocrocyclic bisazetidinones.
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.
Ibrahim
Yehia A
YA
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait. yehiaai@kuc01.kuniv.edu.kw
Al-Azemi
Talal F
TF
Abd El-Halim
Mohamed D
MD
John
Elizabeth
E
D001384:Azetidines / Q000138:chemical synthesis*; D005030:Ethylenes / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism
C116379:2-azetidinone; D001384:Azetidines; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D047028:Macrocyclic Compounds; C008223:ketene