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Acid-Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water
KTH Royal instute of technology, Sweden.
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. KTH Royal instute of technology, Sweden;Univ Massachusetts, USA.
2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 63, p. 14408-14413Article in journal (Refereed) Published
Abstract [en]

The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized alpha-d-manno- and alpha-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis with allyl alcohol could also be achieved with reasonable selectivity. The presence of small quantities (2.5 vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkene isomerization process. The catalytic activity was furthermore retained in the presence of large amounts (0.01 mm) of protein, underlining the potential of this carbon-carbon bond-forming reaction under biological conditions. These results demonstrate the potential of directly using unprotected carbohydrate structures in olefin metathesis reactions under mild conditions compatible with biological systems, and thereby enabling their use in, for example, drug discovery and protein derivatization.

Place, publisher, year, edition, pages
John Wiley & Sons, 2019. Vol. 25, no 63, p. 14408-14413
Keywords [en]
carbene ligands, carbohydrates, homogeneous catalysis, olefin metathesis, synthetic methods
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-90319DOI: 10.1002/chem.201903155ISI: 000496034100021PubMedID: 31390489OAI: oai:DiVA.org:lnu-90319DiVA, id: diva2:1374297
Available from: 2019-11-29 Created: 2019-11-29 Last updated: 2019-11-29Bibliographically approved

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Ramström, Olof

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