Issue 18, 2013
From the journal:

RSC Advances

Sequential Staudinger ketene–iminecycloaddition, RCM approach to polycyclic macrocyclic bisazetidinones†

Yehia A. Ibrahim,*a   Nouria A. Al-Awadi,a   Talal F. Al-Azemi,a   Susan Abrahama  and  Elizabeth Johna  

* Corresponding authors

a Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
E-mail: yehia.ibrahim@ku.edu.kw
Fax: +965-24816482

Abstract

An efficient approach to novel macrocyclic azacrown ethers incorporating two azetidinone rings fused to the macrocycle through the 3,4-positions of the azetidinone rings and two macrocycles fused at 1,3,4-positions of two azetidinone rings was achieved via sequential Staudinger ketene–imine cycloaddition of o-allyloxyphenoxyketene and bis-imines 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 diastereomers. RCM of the latter using Grubbs' II catalyst afforded good yields of the corresponding novel macrocyclic bisazetidinones. Two cis-anti-cis bisazetidinones were readily identified by 1H NMR using Eu(hfc)3 chiral shift reagent and the structure of two macrocycles was established by X-ray crystallography.

Graphical abstract: Sequential Staudinger ketene–imine cycloaddition, RCM approach to polycyclic macrocyclic bisazetidinones

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Article information

DOI
https://doi.org/10.1039/C3RA40649K
Article type
Paper
Submitted
08 Nov 2012
Accepted
08 Feb 2013
First published
08 Feb 2013

RSC Adv., 2013,3, 6408-6416

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Sequential Staudinger ketene–imine cycloaddition, RCM approach to polycyclic macrocyclic bisazetidinones

Y. A. Ibrahim, N. A. Al-Awadi, T. F. Al-Azemi, S. Abraham and E. John, RSC Adv., 2013, 3, 6408 DOI: 10.1039/C3RA40649K

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