Synthesis 2018; 50(05): 1047-1052
DOI: 10.1055/s-0036-1591872
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles­ via Azolium Enolate Intermediates

Sun Li
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Xiang-Yu Chen
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
He Sheng
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Carolina von Essen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Kari Rissanen
b   Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014 JYU, Finland
,
Dieter Enders*
a   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Financial support from the European Research Council (ERC Advanced Grant 320493, ‘DOMINOCAT’) is gratefully acknowledged.
Further Information

Publication History

Received: 24 November 2017

Accepted: 27 November 2017

Publication Date:
20 December 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.

Supporting Information

 
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