title: Asymmetric synthesis of 2,4,5-trisubstituted Δ2-thiazolines.
abstract: Δ(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 Δ(2)-thiazolines. These Δ(2)-thiazolines were synthesized from readily accessible/commercially available α,β-unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.
authors.affiliation: Department of Chemistry, Umeå University, 90187 Umeå, Sweden.
authors.forename: Christoffer
authors.initials: C
authors.lastname: Bengtsson
authors.forename: Hanna
authors.initials: H
authors.lastname: Nelander
authors.forename: Fredrik
authors.initials: F
authors.lastname: Almqvist
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D013844:Thiazoles
keywords: acyl migration; asymmetric synthesis; heterocycles; thiazolines; unnatural amino acids