Asymmetric Synthesis of 2,4,5-Trisubstituted (2)-Thiazolines

(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)-thiazol...

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Veröffentlicht in:Chemistry : a European journal 2013, Vol.19 (30), p.9916
Hauptverfasser: Bengtsson, Christoffer, Nelander, Hanna, Almqvist, Fredrik
Format: Artikel
Sprache:eng
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Zusammenfassung:(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.
ISSN:1521-3765
0947-6539
DOI:10.1002/chem.201301120