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Synthesis 2018; 50(05): 1047-1052
DOI: 10.1055/s-0036-1591872
DOI: 10.1055/s-0036-1591872
paper
N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles via Azolium Enolate Intermediates
Financial support from the European Research Council (ERC Advanced Grant 320493, ‘DOMINOCAT’) is gratefully acknowledged.Weitere Informationen
Publikationsverlauf
Received: 24. November 2017
Accepted: 27. November 2017
Publikationsdatum:
20. Dezember 2017 (online)
Abstract
A highly diastereo- and enantiostereoselective synthesis of bicyclic dihydropyranothiazoles combining a thiazole and δ-lactone skeleton via NHC-catalyzed [4+2] annulation of 5-alkenylthiazolones and α-chloroaldehydes has been developed. The heterocyclic products are formed via azolium enolate intermediates in good yields with high diastereo- and enantistereoselectivities.
Key words
asymmetric synthesis - dihydropyranone thiazole - N-heterocyclic carbene - organocatalysis - [4+2] annulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591872.
- Supporting Information
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