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Synthesis 2015; 47(03): 421-428
DOI: 10.1055/s-0034-1379369
DOI: 10.1055/s-0034-1379369
paper
Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
Further Information
Publication History
Received: 26 September 2014
Accepted after revision: 30 September 2014
Publication Date:
06 November 2014 (online)
Dedicated to Professor Martin Jansen on the occasion of his 70th birthday
Abstract
Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels–Alder reactions of (E)-2-styrylbenzothiazoles with α-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44–97%) with very good to excellent stereoselectivities (up to 9:1 dr, 98% ee) and tolerates quite a range of substituents.
Key words
N-heterocyclic carbenes - organocatalysis - asymmetric synthesis - aza-Diels–Alder reaction - annulationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379369. Included are copies of the 1H and 13C NMR spectra of products 3a–l, HPLC measurements of products 3a–l, and the NOESY spectrum of 3d.
- Supporting Information
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