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

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)-thia...

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Autores principales: Bengtsson, Christoffer, Nelander, Hanna, Almqvist, Fredrik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2013
Materias:
Full Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3784040/
https://www.ncbi.nlm.nih.gov/pubmed/23776083
http://dx.doi.org/10.1002/chem.201301120
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author Bengtsson, Christoffer
Nelander, Hanna
Almqvist, Fredrik
author_facet Bengtsson, Christoffer
Nelander, Hanna
Almqvist, Fredrik
author_sort Bengtsson, Christoffer
collection PubMed
description 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.
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spelling pubmed-37840402013-10-01 Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines Bengtsson, Christoffer Nelander, Hanna Almqvist, Fredrik Chemistry Full Paper 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. WILEY-VCH Verlag 2013-07-22 2013-06-17 /pmc/articles/PMC3784040/ /pubmed/23776083 http://dx.doi.org/10.1002/chem.201301120 Text en © 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes http://creativecommons.org/licenses/by/2.5/ Re-use of this article is permitted in accordance with the Creative Commons Deed, Attribution 2.5, which does not permit commercial exploitation.
spellingShingle Full Paper
Bengtsson, Christoffer
Nelander, Hanna
Almqvist, Fredrik
Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title_full Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title_fullStr Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title_full_unstemmed Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title_short Asymmetric Synthesis of 2,4,5-Trisubstituted Δ(2)-Thiazolines
title_sort asymmetric synthesis of 2,4,5-trisubstituted δ(2)-thiazolines
topic Full Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3784040/
https://www.ncbi.nlm.nih.gov/pubmed/23776083
http://dx.doi.org/10.1002/chem.201301120
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