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Asymmetric Synthesis of 2,4,5‐Trisubstituted Δ 2 ‐Thiazolines
Author(s) -
Bengtsson Christoffer,
Nelander Hanna,
Almqvist Fredrik
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301120
Subject(s) - sharpless asymmetric dihydroxylation , chemistry , dihydroxylation , enantiomer , enantioselective synthesis , enantiomeric excess , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
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.