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Asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through dynamic covalent kinetic resolution
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0001-5298-4310
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2014 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, 3826-3831 p.Article in journal (Refereed) Published
Abstract [en]

The asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through an enzyme-catalyzed, dynamic covalent kinetic resolution strategy is presented. Dynamic hemithioacetal formation combined with intramolecular, lipase-catalyzed lactonization resulted in good conversions with moderate to good enantiomeric excess (ee) for the final products. The process was evaluated for different lipase preparations, solvents, bases, and reaction temperatures, where lipase B from Candida antarctica (CAL-B) proved most efficient. The substrate scope was furthermore explored for a range of aldehyde structures, together with the potential access to nucleoside analog inhibitor core structures.

Place, publisher, year, edition, pages
2014. Vol. 70, no 24, 3826-3831 p.
Keyword [en]
Dynamic chemistry, Dynamic kinetic resolution, Enzyme catalysis, Hemithioacetal formation, Lactonization, Nucleoside analogs
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-147410DOI: 10.1016/j.tet.2014.03.059ISI: 000336710200013Scopus ID: 2-s2.0-84899967956OAI: oai:DiVA.org:kth-147410DiVA: diva2:731617
Note

QC 20140702

Available from: 2014-07-02 Created: 2014-06-27 Last updated: 2017-12-05Bibliographically approved

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Schaufelberger, Fredrik

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