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Asymmetric Synthesis of 2,4,5-Trisubstituted (2)-Thiazolines
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2013 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 30, 9916-9922 p.Article in journal (Refereed) Published
Abstract [en]

(2)-Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5-trisubstituted (2)-thiazolines. These (2)-thiazolines were synthesized from readily accessible/commercially available ,-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an ON acyl migration reaction as key steps. The final products were obtained in good yields with up to 97% enantiomeric excess.

Place, publisher, year, edition, pages
2013. Vol. 19, no 30, 9916-9922 p.
Keyword [en]
acyl migration, asymmetric synthesis, heterocycles, unnatural amino acids, thiazolines
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-79422DOI: 10.1002/chem.201301120ISI: 000321766400029OAI: oai:DiVA.org:umu-79422DiVA: diva2:645451
Available from: 2013-09-04 Created: 2013-08-19 Last updated: 2017-12-06Bibliographically approved

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Bengtsson, ChristofferAlmqvist, Fredrik

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