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Keywords:

  • acyl migration;
  • asymmetric synthesis;
  • heterocycles;
  • unnatural amino acids;
  • thiazolines

Abstract

Δ2-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 Δ2-thiazolines. These Δ2-thiazolines were synthesized from readily accessible/commercially available α,β-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O[RIGHTWARDS ARROW]N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.