Functionalizable stereocontrolled cyclopolyethers by ring-closing metathesis as natural polymer mimics

Alkattan, M., Prunet, J. and Shaver, M. (2018) Functionalizable stereocontrolled cyclopolyethers by ring-closing metathesis as natural polymer mimics. Angewandte Chemie (International Edition), 57(39), pp. 12835-12839. (doi:10.1002/anie.201805113) (PMID:29873428) (PMCID:PMC6175094)

[img]
Preview
Text
163532.pdf - Published Version
Available under License Creative Commons Attribution.

2MB

Abstract

While complex stereoregular cyclic architectures are commonplace in biomacromolecules, they remain rare in synthetic polymer chemistry, limiting the potential to develop synthetic mimics or advanced materials for biomedical applications. Herein we disclose the formation of a stereocontrolled 1,4‐linked six‐membered cyclopolyether prepared by ring‐closing metathesis (RCM). Ru‐mediated RCM, with careful control of catalyst, concentration and temperature, selectively affords the six‐membered ring cyclopolymer. Under optimized reaction conditions, no metathetical degradation, macrocycle or crosslinking was observed. Post‐polymerization modification by dihydroxylation afforded a novel polymer family encompassing a poly(ethylene glycol) backbone and sugar‐like functionalities ("PEGose"). This strategy also paves the way for using RCM as an efficient method to synthesize other stereocontrolled cyclopolymers.

Item Type:Articles
Additional Information:This work was supported by the University of Edinburgh and EaStCHEM, the University of Glasgow and WestCHEM, and EPSRC (Doctoral Training Allocation EP/M506539/1 for M.A.).
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Alkattan, Mr Mohammed and Prunet, Dr Joelle
Authors: Alkattan, M., Prunet, J., and Shaver, M.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Angewandte Chemie (International Edition)
Publisher:Wiley - V C H Verlag GmbH & Co. KGaA
ISSN:1433-7851
ISSN (Online):1521-3773
Published Online:06 June 2018
Copyright Holders:Copyright © 2018 The Authors
First Published:Angewandte Chemie (International Edition) 57(39):1283-12839
Publisher Policy:Reproduced under a Creative Commons License

University Staff: Request a correction | Enlighten Editors: Update this record

Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
678901EPSRC DTG 2014Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M506539/1R&I - RESEARCH STRATEGY & INNOVATION