Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes

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...

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Detalles Bibliográficos
Autores principales: Song, Xiaoxiao, Ni, Qijian, Zhu, Chen, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702348/
https://www.ncbi.nlm.nih.gov/pubmed/26752795
http://dx.doi.org/10.1055/s-0034-1379369
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author Song, Xiaoxiao
Ni, Qijian
Zhu, Chen
Raabe, Gerhard
Enders, Dieter
author_facet Song, Xiaoxiao
Ni, Qijian
Zhu, Chen
Raabe, Gerhard
Enders, Dieter
author_sort Song, Xiaoxiao
collection PubMed
description 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.
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spelling pubmed-47023482016-01-06 Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes Song, Xiaoxiao Ni, Qijian Zhu, Chen Raabe, Gerhard Enders, Dieter Synthesis (Stuttg) Article 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. 2014-11-06 /pmc/articles/PMC4702348/ /pubmed/26752795 http://dx.doi.org/10.1055/s-0034-1379369 Text en License terms: CC BY-NC-ND (http://creativecommons.org/licenses/by-nc-nd/4.0/)
spellingShingle Article
Song, Xiaoxiao
Ni, Qijian
Zhu, Chen
Raabe, Gerhard
Enders, Dieter
Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title_full Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title_fullStr Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title_full_unstemmed Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title_short Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
title_sort asymmetric n-heterocyclic carbene catalyzed annulation of 2-alkenylbenzothiazoles with α-chloro aldehydes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4702348/
https://www.ncbi.nlm.nih.gov/pubmed/26752795
http://dx.doi.org/10.1055/s-0034-1379369
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AT zhuchen asymmetricnheterocycliccarbenecatalyzedannulationof2alkenylbenzothiazoleswithachloroaldehydes
AT raabegerhard asymmetricnheterocycliccarbenecatalyzedannulationof2alkenylbenzothiazoleswithachloroaldehydes
AT endersdieter asymmetricnheterocycliccarbenecatalyzedannulationof2alkenylbenzothiazoleswithachloroaldehydes

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