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Subtilisin integrated artificial plant cell walls as heterogeneous catalysts for asymmetric synthesis of (S)-amides
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8462-4176
2023 (English)In: RSC Advances, E-ISSN 2046-2069, Vol. 13, no 29, p. 19975-19980Article in journal (Refereed) Published
Abstract [en]

Subtilisin integrated artificial plant-cell walls (APCWs) were fabricated by self-assembly using cellulose or nanocellulose as the main component. The resulting APCW catalysts are excellent heterogeneous catalysts for the asymmetric synthesis of (S)-amides. This was demonstrated by the APCW-catalyzed kinetic resolution of several racemic primary amines to give the corresponding (S)-amides in high yields with excellent enantioselectivity. The APCW catalyst can be recycled for multiple reaction cycles without loss of enantioselectivity. The assembled APCW catalyst was also able to cooperate with a homogeneous organoruthenium complex, which allowed for the co-catalytic dynamic kinetic resolution (DKR) of a racemic primary amine to give the corresponding (S)-amide in high yield. The APCW/Ru co-catalysis constitutes the first examples of DKR of chiral primary amines when subtilisin is used as a co-catalyst.

Place, publisher, year, edition, pages
2023. Vol. 13, no 29, p. 19975-19980
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Chemical Sciences
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URN: urn:nbn:se:su:diva-221327DOI: 10.1039/d3ra02193aISI: 001022295400001PubMedID: 37404321Scopus ID: 2-s2.0-85165532562OAI: oai:DiVA.org:su-221327DiVA, id: diva2:1798524
Available from: 2023-09-19 Created: 2023-09-19 Last updated: 2023-09-19Bibliographically approved

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Bäckvall, Jan-E.

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